diff --git a/src/registrar/admin.py b/src/registrar/admin.py
index 1b13d8e74..76fad8975 100644
--- a/src/registrar/admin.py
+++ b/src/registrar/admin.py
@@ -1,18 +1,20 @@
+from datetime import date
 import logging
+
 from django import forms
-from django.db.models.functions import Concat
-from django.http import HttpResponse
+from django.db.models.functions import Concat, Coalesce
+from django.db.models import Value, CharField
+from django.http import HttpResponse, HttpResponseRedirect
 from django.shortcuts import redirect
 from django_fsm import get_available_FIELD_transitions
 from django.contrib import admin, messages
 from django.contrib.auth.admin import UserAdmin as BaseUserAdmin
 from django.contrib.auth.models import Group
 from django.contrib.contenttypes.models import ContentType
-from django.http.response import HttpResponseRedirect
 from django.urls import reverse
+from dateutil.relativedelta import relativedelta  # type: ignore
 from epplibwrapper.errors import ErrorCode, RegistryError
-from registrar.models.domain import Domain
-from registrar.models.user import User
+from registrar.models import Contact, Domain, DomainApplication, DraftDomain, User, Website
 from registrar.utility import csv_export
 from registrar.views.utility.mixins import OrderableFieldsMixin
 from django.contrib.admin.views.main import ORDER_VAR
@@ -23,6 +25,7 @@ from django_fsm import TransitionNotAllowed  # type: ignore
 from django.utils.safestring import mark_safe
 from django.utils.html import escape
 
+
 logger = logging.getLogger(__name__)
 
 
@@ -118,41 +121,52 @@ class CustomLogEntryAdmin(LogEntryAdmin):
 
 
 class AdminSortFields:
-    def get_queryset(db_field):
+    _name_sort = ["first_name", "last_name", "email"]
+
+    # Define a mapping of field names to model querysets and sort expressions.
+    # A dictionary is used for specificity, but the downside is some degree of repetition.
+    # To eliminate this, this list can be generated dynamically but the readability of that
+    # is impacted.
+    sort_mapping = {
+        # == Contact == #
+        "other_contacts": (Contact, _name_sort),
+        "authorizing_official": (Contact, _name_sort),
+        "submitter": (Contact, _name_sort),
+        # == User == #
+        "creator": (User, _name_sort),
+        "user": (User, _name_sort),
+        "investigator": (User, _name_sort),
+        # == Website == #
+        "current_websites": (Website, "website"),
+        "alternative_domains": (Website, "website"),
+        # == DraftDomain == #
+        "requested_domain": (DraftDomain, "name"),
+        # == DomainApplication == #
+        "domain_application": (DomainApplication, "requested_domain__name"),
+        # == Domain == #
+        "domain": (Domain, "name"),
+        "approved_domain": (Domain, "name"),
+    }
+
+    @classmethod
+    def get_queryset(cls, db_field):
         """This is a helper function for formfield_for_manytomany and formfield_for_foreignkey"""
-        # customize sorting
-        if db_field.name in (
-            "other_contacts",
-            "authorizing_official",
-            "submitter",
-        ):
-            # Sort contacts by first_name, then last_name, then email
-            return models.Contact.objects.all().order_by(Concat("first_name", "last_name", "email"))
-        elif db_field.name in ("current_websites", "alternative_domains"):
-            # sort web sites
-            return models.Website.objects.all().order_by("website")
-        elif db_field.name in (
-            "creator",
-            "user",
-            "investigator",
-        ):
-            # Sort users by first_name, then last_name, then email
-            return models.User.objects.all().order_by(Concat("first_name", "last_name", "email"))
-        elif db_field.name in (
-            "domain",
-            "approved_domain",
-        ):
-            # Sort domains by name
-            return models.Domain.objects.all().order_by("name")
-        elif db_field.name in ("requested_domain",):
-            # Sort draft domains by name
-            return models.DraftDomain.objects.all().order_by("name")
-        elif db_field.name in ("domain_application",):
-            # Sort domain applications by name
-            return models.DomainApplication.objects.all().order_by("requested_domain__name")
-        else:
+        queryset_info = cls.sort_mapping.get(db_field.name, None)
+        if queryset_info is None:
             return None
 
+        # Grab the model we want to order, and grab how we want to order it
+        model, order_by = queryset_info
+        match db_field.name:
+            case "investigator":
+                # We should only return users who are staff.
+                return model.objects.filter(is_staff=True).order_by(*order_by)
+            case _:
+                if isinstance(order_by, list) or isinstance(order_by, tuple):
+                    return model.objects.order_by(*order_by)
+                else:
+                    return model.objects.order_by(order_by)
+
 
 class AuditedAdmin(admin.ModelAdmin):
     """Custom admin to make auditing easier."""
@@ -170,9 +184,14 @@ class AuditedAdmin(admin.ModelAdmin):
     def formfield_for_manytomany(self, db_field, request, **kwargs):
         """customize the behavior of formfields with manytomany relationships.  the customized
         behavior includes sorting of objects in lists as well as customizing helper text"""
+
+        # Define a queryset. Note that in the super of this,
+        # a new queryset will only be generated if one does not exist.
+        # Thus, the order in which we define queryset matters.
         queryset = AdminSortFields.get_queryset(db_field)
         if queryset:
             kwargs["queryset"] = queryset
+
         formfield = super().formfield_for_manytomany(db_field, request, **kwargs)
         # customize the help text for all formfields for manytomany
         formfield.help_text = (
@@ -182,11 +201,16 @@ class AuditedAdmin(admin.ModelAdmin):
         return formfield
 
     def formfield_for_foreignkey(self, db_field, request, **kwargs):
-        """customize the behavior of formfields with foreign key relationships.  this will customize
-        the behavior of selects.  customized behavior includes sorting of objects in list"""
+        """Customize the behavior of formfields with foreign key relationships. This will customize
+        the behavior of selects. Customized behavior includes sorting of objects in list."""
+
+        # Define a queryset. Note that in the super of this,
+        # a new queryset will only be generated if one does not exist.
+        # Thus, the order in which we define queryset matters.
         queryset = AdminSortFields.get_queryset(db_field)
         if queryset:
             kwargs["queryset"] = queryset
+
         return super().formfield_for_foreignkey(db_field, request, **kwargs)
 
 
@@ -221,7 +245,6 @@ class ListHeaderAdmin(AuditedAdmin, OrderableFieldsMixin):
             parameter_value: string}
         TODO: convert investigator id to investigator username
         """
-
         filters = []
         # Retrieve the filter parameters
         for param in request.GET.keys():
@@ -265,6 +288,14 @@ class UserContactInline(admin.StackedInline):
 class MyUserAdmin(BaseUserAdmin):
     """Custom user admin class to use our inlines."""
 
+    class Meta:
+        """Contains meta information about this class"""
+
+        model = models.User
+        fields = "__all__"
+
+    _meta = Meta()
+
     inlines = [UserContactInline]
 
     list_display = (
@@ -353,6 +384,42 @@ class MyUserAdmin(BaseUserAdmin):
     # in autocomplete_fields for user
     ordering = ["first_name", "last_name", "email"]
 
+    def get_search_results(self, request, queryset, search_term):
+        """
+        Override for get_search_results. This affects any upstream model using autocomplete_fields,
+        such as DomainApplication. This is because autocomplete_fields uses an API call to fetch data,
+        and this fetch comes from this method.
+        """
+        # Custom filtering logic
+        queryset, use_distinct = super().get_search_results(request, queryset, search_term)
+
+        # If we aren't given a request to modify, we shouldn't try to
+        if request is None or not hasattr(request, "GET"):
+            return queryset, use_distinct
+
+        # Otherwise, lets modify it!
+        request_get = request.GET
+
+        # The request defines model name and field name.
+        # For instance, model_name could be "DomainApplication"
+        # and field_name could be "investigator".
+        model_name = request_get.get("model_name", None)
+        field_name = request_get.get("field_name", None)
+
+        # Make sure we're only modifying requests from these models.
+        models_to_target = {"domainapplication"}
+        if model_name in models_to_target:
+            # Define rules per field
+            match field_name:
+                case "investigator":
+                    # We should not display investigators who don't have a staff role
+                    queryset = queryset.filter(is_staff=True)
+                case _:
+                    # In the default case, do nothing
+                    pass
+
+        return queryset, use_distinct
+
     # Let's define First group
     # (which should in theory be the ONLY group)
     def group(self, obj):
@@ -417,6 +484,9 @@ class ContactAdmin(ListHeaderAdmin):
         "contact",
         "email",
     ]
+    # this ordering effects the ordering of results
+    # in autocomplete_fields for user
+    ordering = ["first_name", "last_name", "email"]
 
     # We name the custom prop 'contact' because linter
     # is not allowing a short_description attr on it
@@ -752,8 +822,23 @@ class DomainApplicationAdmin(ListHeaderAdmin):
             """Lookup reimplementation, gets users of is_staff.
             Returns a list of tuples consisting of (user.id, user)
             """
-            privileged_users = User.objects.filter(is_staff=True).order_by("first_name", "last_name", "email")
-            return [(user.id, user) for user in privileged_users]
+            # Select all investigators that are staff, then order by name and email
+            privileged_users = (
+                DomainApplication.objects.select_related("investigator")
+                .filter(investigator__is_staff=True)
+                .order_by("investigator__first_name", "investigator__last_name", "investigator__email")
+            )
+
+            # Annotate the full name and return a values list that lookups can use
+            privileged_users_annotated = privileged_users.annotate(
+                full_name=Coalesce(
+                    Concat("investigator__first_name", Value(" "), "investigator__last_name", output_field=CharField()),
+                    "investigator__email",
+                    output_field=CharField(),
+                )
+            ).values_list("investigator__id", "full_name")
+
+            return privileged_users_annotated
 
         def queryset(self, request, queryset):
             """Custom queryset implementation, filters by investigator"""
@@ -853,26 +938,19 @@ class DomainApplicationAdmin(ListHeaderAdmin):
         "anything_else",
         "is_policy_acknowledged",
     ]
-
+    autocomplete_fields = [
+        "approved_domain",
+        "requested_domain",
+        "submitter",
+        "creator",
+        "authorizing_official",
+        "investigator",
+    ]
     filter_horizontal = ("current_websites", "alternative_domains", "other_contacts")
 
     # Table ordering
     ordering = ["requested_domain__name"]
 
-    # lists in filter_horizontal are not sorted properly, sort them
-    # by website
-    def formfield_for_manytomany(self, db_field, request, **kwargs):
-        if db_field.name in ("current_websites", "alternative_domains"):
-            kwargs["queryset"] = models.Website.objects.all().order_by("website")  # Sort websites
-        return super().formfield_for_manytomany(db_field, request, **kwargs)
-
-    def formfield_for_foreignkey(self, db_field, request, **kwargs):
-        # Removes invalid investigator options from the investigator dropdown
-        if db_field.name == "investigator":
-            kwargs["queryset"] = User.objects.filter(is_staff=True)
-            return db_field.formfield(**kwargs)
-        return super().formfield_for_foreignkey(db_field, request, **kwargs)
-
     # Trigger action when a fieldset is changed
     def save_model(self, request, obj, form, change):
         if obj and obj.creator.status != models.User.RESTRICTED:
@@ -957,7 +1035,6 @@ class DomainApplicationAdmin(ListHeaderAdmin):
         admin user permissions and the application creator's status, so
         we'll use the baseline readonly_fields and extend it as needed.
         """
-
         readonly_fields = list(self.readonly_fields)
 
         # Check if the creator is restricted
@@ -1035,8 +1112,8 @@ class DomainInformationInline(admin.StackedInline):
         return formfield
 
     def formfield_for_foreignkey(self, db_field, request, **kwargs):
-        """customize the behavior of formfields with foreign key relationships.  this will customize
-        the behavior of selects.  customized behavior includes sorting of objects in list"""
+        """Customize the behavior of formfields with foreign key relationships. This will customize
+        the behavior of selects. Customized behavior includes sorting of objects in list."""
         queryset = AdminSortFields.get_queryset(db_field)
         if queryset:
             kwargs["queryset"] = queryset
@@ -1090,6 +1167,26 @@ class DomainAdmin(ListHeaderAdmin):
     # Table ordering
     ordering = ["name"]
 
+    def changeform_view(self, request, object_id=None, form_url="", extra_context=None):
+        """Custom changeform implementation to pass in context information"""
+        if extra_context is None:
+            extra_context = {}
+
+        # Pass in what the an extended expiration date would be for the expiration date modal
+        if object_id is not None:
+            domain = Domain.objects.get(pk=object_id)
+            years_to_extend_by = self._get_calculated_years_for_exp_date(domain)
+            curr_exp_date = domain.registry_expiration_date
+            if curr_exp_date < date.today():
+                extra_context["extended_expiration_date"] = date.today() + relativedelta(years=years_to_extend_by)
+            else:
+                new_date = domain.registry_expiration_date + relativedelta(years=years_to_extend_by)
+                extra_context["extended_expiration_date"] = new_date
+        else:
+            extra_context["extended_expiration_date"] = None
+
+        return super().changeform_view(request, object_id, form_url, extra_context)
+
     def export_data_type(self, request):
         # match the CSV example with all the fields
         response = HttpResponse(content_type="text/csv")
@@ -1148,6 +1245,7 @@ class DomainAdmin(ListHeaderAdmin):
             "_edit_domain": self.do_edit_domain,
             "_delete_domain": self.do_delete_domain,
             "_get_status": self.do_get_status,
+            "_extend_expiration_date": self.do_extend_expiration_date,
         }
 
         # Check which action button was pressed and call the corresponding function
@@ -1158,6 +1256,81 @@ class DomainAdmin(ListHeaderAdmin):
         # If no matching action button is found, return the super method
         return super().response_change(request, obj)
 
+    def do_extend_expiration_date(self, request, obj):
+        """Extends a domains expiration date by one year from the current date"""
+
+        # Make sure we're dealing with a Domain
+        if not isinstance(obj, Domain):
+            self.message_user(request, "Object is not of type Domain.", messages.ERROR)
+            return None
+
+        years = self._get_calculated_years_for_exp_date(obj)
+
+        # Renew the domain.
+        try:
+            obj.renew_domain(length=years)
+            self.message_user(
+                request,
+                "Successfully extended the expiration date.",
+            )
+        except RegistryError as err:
+            if err.is_connection_error():
+                error_message = "Error connecting to the registry."
+            else:
+                error_message = f"Error extending this domain: {err}."
+            self.message_user(request, error_message, messages.ERROR)
+        except KeyError:
+            # In normal code flow, a keyerror can only occur when
+            # fresh data can't be pulled from the registry, and thus there is no cache.
+            self.message_user(
+                request,
+                "Error connecting to the registry. No expiration date was found.",
+                messages.ERROR,
+            )
+        except Exception as err:
+            logger.error(err, stack_info=True)
+            self.message_user(request, "Could not delete: An unspecified error occured", messages.ERROR)
+
+        return HttpResponseRedirect(".")
+
+    def _get_calculated_years_for_exp_date(self, obj, extension_period: int = 1):
+        """Given the current date, an extension period, and a registry_expiration_date
+        on the domain object, calculate the number of years needed to extend the
+        current expiration date by the extension period.
+        """
+        # Get the date we want to update to
+        desired_date = self._get_current_date() + relativedelta(years=extension_period)
+
+        # Grab the current expiration date
+        try:
+            exp_date = obj.registry_expiration_date
+        except KeyError:
+            # if no expiration date from registry, set it to today
+            logger.warning("current expiration date not set; setting to today")
+            exp_date = self._get_current_date()
+
+        # If the expiration date is super old (2020, for example), we need to
+        # "catch up" to the current year, so we add the difference.
+        # If both years match, then lets just proceed as normal.
+        calculated_exp_date = exp_date + relativedelta(years=extension_period)
+
+        year_difference = desired_date.year - exp_date.year
+
+        years = extension_period
+        if desired_date > calculated_exp_date:
+            # Max probably isn't needed here (no code flow), but it guards against negative and 0.
+            # In both of those cases, we just want to extend by the extension_period.
+            years = max(extension_period, year_difference)
+
+        return years
+
+    # Workaround for unit tests, as we cannot mock date directly.
+    # it is immutable. Rather than dealing with a convoluted workaround,
+    # lets wrap this in a function.
+    def _get_current_date(self):
+        """Gets the current date"""
+        return date.today()
+
     def do_delete_domain(self, request, obj):
         if not isinstance(obj, Domain):
             # Could be problematic if the type is similar,
@@ -1316,6 +1489,10 @@ class DraftDomainAdmin(ListHeaderAdmin):
     search_fields = ["name"]
     search_help_text = "Search by draft domain name."
 
+    # this ordering effects the ordering of results
+    # in autocomplete_fields for user
+    ordering = ["name"]
+
 
 class VerifiedByStaffAdmin(ListHeaderAdmin):
     list_display = ("email", "requestor", "truncated_notes", "created_at")
diff --git a/src/registrar/assets/js/get-gov-admin.js b/src/registrar/assets/js/get-gov-admin.js
index 9239a0488..fc6af408a 100644
--- a/src/registrar/assets/js/get-gov-admin.js
+++ b/src/registrar/assets/js/get-gov-admin.js
@@ -23,6 +23,33 @@ function openInNewTab(el, removeAttribute = false){
 // <<>><<>><<>><<>><<>><<>><<>><<>><<>><<>><<>><<>><<>><<>><<>>
 // Initialization code.
 
+/** An IIFE for pages in DjangoAdmin that use modals.
+ * Dja strips out form elements, and modals generate their content outside
+ * of the current form scope, so we need to "inject" these inputs.
+*/
+(function (){
+    function createPhantomModalFormButtons(){
+        let submitButtons = document.querySelectorAll('.usa-modal button[type="submit"]');
+        form = document.querySelector("form")
+        submitButtons.forEach((button) => {
+
+            let input = document.createElement("input");
+            input.type = "submit";
+            input.name = button.name;
+            input.value = button.value;
+            input.style.display = "none"
+
+            // Add the hidden input to the form
+            form.appendChild(input);
+            button.addEventListener("click", () => {
+                console.log("clicking")
+                input.click();
+            })
+        })
+    }
+
+    createPhantomModalFormButtons();
+})();
 /** An IIFE for pages in DjangoAdmin which may need custom JS implementation.
  * Currently only appends target="_blank" to the domain_form object,
  * but this can be expanded.
@@ -41,8 +68,8 @@ function openInNewTab(el, removeAttribute = false){
         let domainFormElement = document.getElementById("domain_form");
         let domainSubmitButton = document.getElementById("manageDomainSubmitButton");
         if(domainSubmitButton && domainFormElement){
-          domainSubmitButton.addEventListener("mouseover", () => openInNewTab(domainFormElement, true));
-          domainSubmitButton.addEventListener("mouseout", () => openInNewTab(domainFormElement, false));
+            domainSubmitButton.addEventListener("mouseover", () => openInNewTab(domainFormElement, true));
+            domainSubmitButton.addEventListener("mouseout", () => openInNewTab(domainFormElement, false));
         }
     }
 
diff --git a/src/registrar/assets/sass/_theme/_admin.scss b/src/registrar/assets/sass/_theme/_admin.scss
index 760c4f13a..b57c6a015 100644
--- a/src/registrar/assets/sass/_theme/_admin.scss
+++ b/src/registrar/assets/sass/_theme/_admin.scss
@@ -183,6 +183,10 @@ h1, h2, h3,
 .submit-row div.spacer {
     flex-grow: 1;
 }
+.submit-row .mini-spacer{
+    margin-left: 2px;
+    margin-right: 2px;
+}
 .submit-row span {
     margin-top: units(1);
 }
@@ -270,3 +274,31 @@ h1, h2, h3,
         margin: 0!important;
     }
 }
+
+// Hides the "clear" button on autocomplete, as we already have one to use
+.select2-selection__clear {
+    display: none;
+}
+
+// Fixes a display issue where the list was entirely white, or had too much whitespace
+.select2-dropdown {
+    display: inline-grid !important;
+}
+
+input.admin-confirm-button {
+    text-transform: none;
+}
+
+// Button groups in /admin incorrectly have bullets.
+// Remove that!
+.usa-modal__footer .usa-button-group__item {
+    list-style-type: none;
+}
+
+// USWDS media checks are overzealous in this situation,
+// we should manually define this behaviour.
+@media (max-width: 768px) {
+    .button-list-mobile {
+        display: contents !important;
+    }
+}
diff --git a/src/registrar/models/domain.py b/src/registrar/models/domain.py
index 7ebe3dc34..020ba43c0 100644
--- a/src/registrar/models/domain.py
+++ b/src/registrar/models/domain.py
@@ -265,15 +265,17 @@ class Domain(TimeStampedModel, DomainHelper):
 
         Default length and unit of time are 1 year.
         """
-        # if no expiration date from registry, set to today
+
+        # If no date is specified, grab the registry_expiration_date
         try:
-            cur_exp_date = self.registry_expiration_date
+            exp_date = self.registry_expiration_date
         except KeyError:
+            # if no expiration date from registry, set it to today
             logger.warning("current expiration date not set; setting to today")
-            cur_exp_date = date.today()
+            exp_date = date.today()
 
         # create RenewDomain request
-        request = commands.RenewDomain(name=self.name, cur_exp_date=cur_exp_date, period=epp.Period(length, unit))
+        request = commands.RenewDomain(name=self.name, cur_exp_date=exp_date, period=epp.Period(length, unit))
 
         try:
             # update expiration date in registry, and set the updated
diff --git a/src/registrar/models/domain_information.py b/src/registrar/models/domain_information.py
index acaa330bb..1a50efe2c 100644
--- a/src/registrar/models/domain_information.py
+++ b/src/registrar/models/domain_information.py
@@ -255,6 +255,14 @@ class DomainInformation(TimeStampedModel):
                 else:
                     da_many_to_many_dict[field] = getattr(domain_application, field).all()
 
+        # This will not happen in normal code flow, but having some redundancy doesn't hurt.
+        # da_dict should not have "id" under any circumstances.
+        # If it does have it, then this indicates that common_fields is overzealous in the data
+        # that it is returning. Try looking in DomainHelper.get_common_fields.
+        if "id" in da_dict:
+            logger.warning("create_from_da() -> Found attribute 'id' when trying to create")
+            da_dict.pop("id", None)
+
         # Create a placeholder DomainInformation object
         domain_info = DomainInformation(**da_dict)
 
diff --git a/src/registrar/models/utility/domain_helper.py b/src/registrar/models/utility/domain_helper.py
index 230b23e16..9e3559676 100644
--- a/src/registrar/models/utility/domain_helper.py
+++ b/src/registrar/models/utility/domain_helper.py
@@ -180,8 +180,8 @@ class DomainHelper:
         """
 
         # Get a list of the existing fields on model_1 and model_2
-        model_1_fields = set(field.name for field in model_1._meta.get_fields() if field != "id")
-        model_2_fields = set(field.name for field in model_2._meta.get_fields() if field != "id")
+        model_1_fields = set(field.name for field in model_1._meta.get_fields() if field.name != "id")
+        model_2_fields = set(field.name for field in model_2._meta.get_fields() if field.name != "id")
 
         # Get the fields that exist on both DomainApplication and DomainInformation
         common_fields = model_1_fields & model_2_fields
diff --git a/src/registrar/models/utility/generic_helper.py b/src/registrar/models/utility/generic_helper.py
new file mode 100644
index 000000000..01d4e6b33
--- /dev/null
+++ b/src/registrar/models/utility/generic_helper.py
@@ -0,0 +1,37 @@
+"""This file contains general purpose helpers that don't belong in any specific location"""
+
+import time
+import logging
+
+
+logger = logging.getLogger(__name__)
+
+
+class Timer:
+    """
+    This class is used to measure execution time for performance profiling.
+    __enter__ and __exit__ is used such that you can wrap any code you want
+    around a with statement. After this exits, logger.info will print
+    the execution time in seconds.
+
+    Note that this class does not account for general randomness as more
+    robust libraries do, so there is some tiny amount of latency involved
+    in using this, but it is minimal enough that for most applications it is not
+    noticable.
+
+    Usage:
+    with Timer():
+        ...some code
+    """
+
+    def __enter__(self):
+        """Starts the timer"""
+        self.start = time.time()
+        # This allows usage of the instance within the with block
+        return self
+
+    def __exit__(self, *args):
+        """Ends the timer and logs what happened"""
+        self.end = time.time()
+        self.duration = self.end - self.start
+        logger.info(f"Execution time: {self.duration} seconds")
diff --git a/src/registrar/templates/admin/base_site.html b/src/registrar/templates/admin/base_site.html
index f9ff23455..73e9ba1f0 100644
--- a/src/registrar/templates/admin/base_site.html
+++ b/src/registrar/templates/admin/base_site.html
@@ -18,11 +18,12 @@
   <link rel="apple-touch-icon" size="180x180" 
   href="{% static 'img/registrar/favicons/favicon-180.png' %}"
   >
+  <script src="{% static 'js/uswds-init.min.js' %}" defer></script>
+  <script src="{% static 'js/uswds.min.js' %}" defer></script>
   <script type="application/javascript" src="{% static 'js/get-gov-admin.js' %}" defer></script>
 {% endblock %}
 
 {% block title %}{% if subtitle %}{{ subtitle }} | {% endif %}{{ title }} | {{ site_title|default:_('Django site admin') }}{% endblock %}
-
 {% block extrastyle %}{{ block.super }}
 <link rel="stylesheet" type="text/css" href="{% static 'css/styles.css' %}" />
 {% endblock %}
diff --git a/src/registrar/templates/django/admin/domain_change_form.html b/src/registrar/templates/django/admin/domain_change_form.html
index c4461d07f..67c5ac291 100644
--- a/src/registrar/templates/django/admin/domain_change_form.html
+++ b/src/registrar/templates/django/admin/domain_change_form.html
@@ -2,21 +2,117 @@
 {% load i18n static %}
 
 {% block field_sets %}
-    <div class="submit-row">
-        <input id="manageDomainSubmitButton" type="submit" value="Manage domain" name="_edit_domain">
-        <input type="submit" value="Get registry status" name="_get_status">
-        <div class="spacer"></div>
-        {% if original.state == original.State.READY %}
-        <input type="submit" value="Place hold" name="_place_client_hold" class="custom-link-button">
-        {% elif original.state == original.State.ON_HOLD %}
-        <input type="submit" value="Remove hold" name="_remove_client_hold" class="custom-link-button">
-        {% endif %}
-        {% if original.state == original.State.READY or original.state == original.State.ON_HOLD %}
-        <span> | </span>
-        {% endif %}
-        {% if original.state != original.State.DELETED %}
-        <input type="submit" value="Remove from registry" name="_delete_domain" class="custom-link-button">
+    <div class="display-flex flex-row flex-justify submit-row">
+        <div class="flex-align-self-start button-list-mobile">
+            <input id="manageDomainSubmitButton" type="submit" value="Manage domain" name="_edit_domain">
+            {# Dja has margin styles defined on inputs as is. Lets work with it, rather than fight it. #}
+            <span class="mini-spacer"></span>
+            <input type="submit" value="Get registry status" name="_get_status">
+        </div>
+        <div class="desktop:flex-align-self-end">
+            {% if original.state != original.State.DELETED %}
+            <a
+            class="text-middle"
+            href="#toggle-extend-expiration-alert"
+            aria-controls="toggle-extend-expiration-alert"
+            data-open-modal
+            >
+                Extend expiration date
+            </a>
+            <span class="margin-left-05 margin-right-05 text-middle"> | </span>
+            {% endif %}
+            {% if original.state == original.State.READY %}
+            <input type="submit" value="Place hold" name="_place_client_hold" class="custom-link-button">
+            {% elif original.state == original.State.ON_HOLD %}
+            <input type="submit" value="Remove hold" name="_remove_client_hold" class="custom-link-button">
+            {% endif %}
+            {% if original.state == original.State.READY or original.state == original.State.ON_HOLD %}
+            <span class="margin-left-05 margin-right-05 text-middle"> | </span>
+            {% endif %}
+            {% if original.state != original.State.DELETED %}
+            <input type="submit" value="Remove from registry" name="_delete_domain" class="custom-link-button">
         {% endif %}
+        </div>
     </div>
     {{ block.super }}
 {% endblock %}
+
+{% block submit_buttons_bottom %}
+    {% comment %}
+    Modals behave very weirdly in django admin.
+    They tend to "strip out" any injected form elements, leaving only the main form.
+    In addition, USWDS handles modals by first destroying the element, then repopulating it toward the end of the page.
+    In effect, this means that the modal is not, and cannot, be surrounded by any form element at compile time.
+
+    The current workaround for this is to use javascript to inject a hidden input, and bind submit of that
+    element to the click of the confirmation button within this modal.
+
+    This is controlled by the class `dja-form-placeholder` on the button.
+
+    In addition, the modal element MUST be placed low in the DOM. The script loads slower on DJA than on other portions
+    of the application, so this means that it will briefly "populate", causing unintended visual effects.
+    {% endcomment %}
+    <div
+    class="usa-modal"
+    id="toggle-extend-expiration-alert"
+    aria-labelledby="Are you sure you want to extend the expiration date?"
+    aria-describedby="This expiration date will be extended."
+    >
+        <div class="usa-modal__content">
+            <div class="usa-modal__main">
+                <h2 class="usa-modal__heading" id="modal-1-heading">
+                    Are you sure you want to extend the expiration date?
+                </h2>
+                <div class="usa-prose">
+                    <p>
+                        This will extend the expiration date by one year.
+                        {# Acts as a <br> #}
+                        <div class="display-inline"></div>
+                        This action cannot be undone.
+                    </p>
+                    <p>
+                        Domain: <b>{{ original.name }}</b>
+                        {# Acts as a <br> #}
+                        <div class="display-inline"></div>
+                        New expiration date: <b>{{ extended_expiration_date }}</b>
+                        {{test}}
+                    </p>
+                </div>
+        
+                <div class="usa-modal__footer">
+                    <ul class="usa-button-group">
+                        <li class="usa-button-group__item">
+                            <button
+                            type="submit" 
+                            class="usa-button dja-form-placeholder" 
+                            name="_extend_expiration_date"
+                            >
+                                Yes, extend date
+                            </button>
+                        </li>
+                        <li class="usa-button-group__item">
+                            <button
+                            type="button"
+                            class="usa-button usa-button--unstyled padding-105 text-center"
+                            data-close-modal
+                            >
+                                Cancel
+                            </button>
+                        </li>
+                    </ul>
+                </div>
+            </div>
+            <button
+            type="button"
+            class="usa-button usa-modal__close"
+            aria-label="Close this window"
+            data-close-modal
+            >
+                <svg class="usa-icon" aria-hidden="true" focusable="false" role="img">
+                    <use xlink:href="{%static 'img/sprite.svg'%}#close"></use>
+                </svg>
+            </button>
+        </div>
+    </div>
+{{ block.super }}
+{% endblock %}
\ No newline at end of file
diff --git a/src/registrar/templates/home.html b/src/registrar/templates/home.html
index a79065f50..93f1243ea 100644
--- a/src/registrar/templates/home.html
+++ b/src/registrar/templates/home.html
@@ -15,6 +15,7 @@
   {% endblock %}
   <h1>Manage your domains</h2>
 
+
   <p class="margin-top-4">
     <a href="{% url 'application:' %}" class="usa-button"
     >
diff --git a/src/registrar/tests/common.py b/src/registrar/tests/common.py
index 2865bf5c5..17833d689 100644
--- a/src/registrar/tests/common.py
+++ b/src/registrar/tests/common.py
@@ -231,6 +231,7 @@ class AuditedAdminMockData:
             first_name="{} first_name:{}".format(item_name, short_hand),
             last_name="{} last_name:{}".format(item_name, short_hand),
             username="{} username:{}".format(item_name + str(uuid.uuid4())[:8], short_hand),
+            is_staff=True,
         )[0]
         return user
 
@@ -921,6 +922,11 @@ class MockEppLib(TestCase):
         ex_date=datetime.date(2023, 5, 25),
     )
 
+    mockButtonRenewedDomainExpDate = fakedEppObject(
+        "fake.gov",
+        ex_date=datetime.date(2025, 5, 25),
+    )
+
     mockDnsNeededRenewedDomainExpDate = fakedEppObject(
         "fakeneeded.gov",
         ex_date=datetime.date(2023, 2, 15),
@@ -1049,11 +1055,19 @@ class MockEppLib(TestCase):
                 res_data=[self.mockMaximumRenewedDomainExpDate],
                 code=ErrorCode.COMMAND_COMPLETED_SUCCESSFULLY,
             )
-        else:
-            return MagicMock(
-                res_data=[self.mockRenewedDomainExpDate],
-                code=ErrorCode.COMMAND_COMPLETED_SUCCESSFULLY,
-            )
+        elif getattr(_request, "name", None) == "fake.gov":
+            period = getattr(_request, "period", None)
+            extension_period = getattr(period, "length", None)
+            if extension_period == 2:
+                return MagicMock(
+                    res_data=[self.mockButtonRenewedDomainExpDate],
+                    code=ErrorCode.COMMAND_COMPLETED_SUCCESSFULLY,
+                )
+            else:
+                return MagicMock(
+                    res_data=[self.mockRenewedDomainExpDate],
+                    code=ErrorCode.COMMAND_COMPLETED_SUCCESSFULLY,
+                )
 
     def mockInfoDomainCommands(self, _request, cleaned):
         request_name = getattr(_request, "name", None)
diff --git a/src/registrar/tests/test_admin.py b/src/registrar/tests/test_admin.py
index 4e449ca5d..4225f82c5 100644
--- a/src/registrar/tests/test_admin.py
+++ b/src/registrar/tests/test_admin.py
@@ -1,6 +1,8 @@
+from datetime import date
 from django.test import TestCase, RequestFactory, Client
 from django.contrib.admin.sites import AdminSite
 from contextlib import ExitStack
+from django_webtest import WebTest  # type: ignore
 from django.contrib import messages
 from django.urls import reverse
 from registrar.admin import (
@@ -35,7 +37,7 @@ from .common import (
 )
 from django.contrib.sessions.backends.db import SessionStore
 from django.contrib.auth import get_user_model
-from unittest.mock import patch
+from unittest.mock import ANY, call, patch
 from unittest import skip
 
 from django.conf import settings
@@ -45,7 +47,11 @@ import logging
 logger = logging.getLogger(__name__)
 
 
-class TestDomainAdmin(MockEppLib):
+class TestDomainAdmin(MockEppLib, WebTest):
+    # csrf checks do not work with WebTest.
+    # We disable them here. TODO for another ticket.
+    csrf_checks = False
+
     def setUp(self):
         self.site = AdminSite()
         self.admin = DomainAdmin(model=Domain, admin_site=self.site)
@@ -53,8 +59,177 @@ class TestDomainAdmin(MockEppLib):
         self.superuser = create_superuser()
         self.staffuser = create_user()
         self.factory = RequestFactory()
+        self.app.set_user(self.superuser.username)
+        self.client.force_login(self.superuser)
         super().setUp()
 
+    @skip("TODO for another ticket. This test case is grabbing old db data.")
+    @patch("registrar.admin.DomainAdmin._get_current_date", return_value=date(2024, 1, 1))
+    def test_extend_expiration_date_button(self, mock_date_today):
+        """
+        Tests if extend_expiration_date button extends correctly
+        """
+
+        # Create a ready domain with a preset expiration date
+        domain, _ = Domain.objects.get_or_create(name="fake.gov", state=Domain.State.READY)
+
+        response = self.app.get(reverse("admin:registrar_domain_change", args=[domain.pk]))
+
+        # Make sure the ex date is what we expect it to be
+        domain_ex_date = Domain.objects.get(id=domain.id).expiration_date
+        self.assertEqual(domain_ex_date, date(2023, 5, 25))
+
+        # Make sure that the page is loading as expected
+        self.assertEqual(response.status_code, 200)
+        self.assertContains(response, domain.name)
+        self.assertContains(response, "Extend expiration date")
+
+        # Grab the form to submit
+        form = response.forms["domain_form"]
+
+        with patch("django.contrib.messages.add_message") as mock_add_message:
+            # Submit the form
+            response = form.submit("_extend_expiration_date")
+
+            # Follow the response
+            response = response.follow()
+
+        # refresh_from_db() does not work for objects with protected=True.
+        # https://github.com/viewflow/django-fsm/issues/89
+        new_domain = Domain.objects.get(id=domain.id)
+
+        # Check that the current expiration date is what we expect
+        self.assertEqual(new_domain.expiration_date, date(2025, 5, 25))
+
+        # Assert that everything on the page looks correct
+        self.assertEqual(response.status_code, 200)
+        self.assertContains(response, domain.name)
+        self.assertContains(response, "Extend expiration date")
+
+        # Ensure the message we recieve is in line with what we expect
+        expected_message = "Successfully extended the expiration date."
+        expected_call = call(
+            # The WGSI request doesn't need to be tested
+            ANY,
+            messages.INFO,
+            expected_message,
+            extra_tags="",
+            fail_silently=False,
+        )
+        mock_add_message.assert_has_calls([expected_call], 1)
+
+    @patch("registrar.admin.DomainAdmin._get_current_date", return_value=date(2024, 1, 1))
+    def test_extend_expiration_date_button_epp(self, mock_date_today):
+        """
+        Tests if extend_expiration_date button sends the right epp command
+        """
+
+        # Create a ready domain with a preset expiration date
+        domain, _ = Domain.objects.get_or_create(name="fake.gov", state=Domain.State.READY)
+
+        response = self.app.get(reverse("admin:registrar_domain_change", args=[domain.pk]))
+
+        # Make sure that the page is loading as expected
+        self.assertEqual(response.status_code, 200)
+        self.assertContains(response, domain.name)
+        self.assertContains(response, "Extend expiration date")
+
+        # Grab the form to submit
+        form = response.forms["domain_form"]
+
+        with patch("django.contrib.messages.add_message") as mock_add_message:
+            with patch("registrar.models.Domain.renew_domain") as renew_mock:
+                # Submit the form
+                response = form.submit("_extend_expiration_date")
+
+                # Follow the response
+                response = response.follow()
+
+        # This value is based off of the current year - the expiration date.
+        # We "freeze" time to 2024, so 2024 - 2023 will always result in an
+        # "extension" of 2, as that will be one year of extension from that date.
+        extension_length = 2
+
+        # Assert that it is calling the function with the right extension length.
+        # We only need to test the value that EPP sends, as we can assume the other
+        # test cases cover the "renew" function.
+        renew_mock.assert_has_calls([call(length=extension_length)], any_order=False)
+
+        # We should not make duplicate calls
+        self.assertEqual(renew_mock.call_count, 1)
+
+        # Assert that everything on the page looks correct
+        self.assertEqual(response.status_code, 200)
+        self.assertContains(response, domain.name)
+        self.assertContains(response, "Extend expiration date")
+
+        # Ensure the message we recieve is in line with what we expect
+        expected_message = "Successfully extended the expiration date."
+        expected_call = call(
+            # The WGSI request doesn't need to be tested
+            ANY,
+            messages.INFO,
+            expected_message,
+            extra_tags="",
+            fail_silently=False,
+        )
+        mock_add_message.assert_has_calls([expected_call], 1)
+
+    @patch("registrar.admin.DomainAdmin._get_current_date", return_value=date(2023, 1, 1))
+    def test_extend_expiration_date_button_date_matches_epp(self, mock_date_today):
+        """
+        Tests if extend_expiration_date button sends the right epp command
+        when the current year matches the expiration date
+        """
+
+        # Create a ready domain with a preset expiration date
+        domain, _ = Domain.objects.get_or_create(name="fake.gov", state=Domain.State.READY)
+
+        response = self.app.get(reverse("admin:registrar_domain_change", args=[domain.pk]))
+
+        # Make sure that the page is loading as expected
+        self.assertEqual(response.status_code, 200)
+        self.assertContains(response, domain.name)
+        self.assertContains(response, "Extend expiration date")
+
+        # Grab the form to submit
+        form = response.forms["domain_form"]
+
+        with patch("django.contrib.messages.add_message") as mock_add_message:
+            with patch("registrar.models.Domain.renew_domain") as renew_mock:
+                # Submit the form
+                response = form.submit("_extend_expiration_date")
+
+                # Follow the response
+                response = response.follow()
+
+        extension_length = 1
+
+        # Assert that it is calling the function with the right extension length.
+        # We only need to test the value that EPP sends, as we can assume the other
+        # test cases cover the "renew" function.
+        renew_mock.assert_has_calls([call(length=extension_length)], any_order=False)
+
+        # We should not make duplicate calls
+        self.assertEqual(renew_mock.call_count, 1)
+
+        # Assert that everything on the page looks correct
+        self.assertEqual(response.status_code, 200)
+        self.assertContains(response, domain.name)
+        self.assertContains(response, "Extend expiration date")
+
+        # Ensure the message we recieve is in line with what we expect
+        expected_message = "Successfully extended the expiration date."
+        expected_call = call(
+            # The WGSI request doesn't need to be tested
+            ANY,
+            messages.INFO,
+            expected_message,
+            extra_tags="",
+            fail_silently=False,
+        )
+        mock_add_message.assert_has_calls([expected_call], 1)
+
     def test_short_org_name_in_domains_list(self):
         """
         Make sure the short name is displaying in admin on the list page
@@ -1212,8 +1387,17 @@ class TestDomainApplicationAdmin(MockEppLib):
             investigator_field = DomainApplication._meta.get_field("investigator")
 
             # We should only be displaying staff users, in alphabetical order
-            expected_dropdown = list(User.objects.filter(is_staff=True))
-            current_dropdown = list(self.admin.formfield_for_foreignkey(investigator_field, request).queryset)
+            sorted_fields = ["first_name", "last_name", "email"]
+            expected_dropdown = list(User.objects.filter(is_staff=True).order_by(*sorted_fields))
+
+            # Grab the current dropdown. We do an API call to autocomplete to get this info.
+            application_queryset = self.admin.formfield_for_foreignkey(investigator_field, request).queryset
+            user_request = self.factory.post(
+                "/admin/autocomplete/?app_label=registrar&model_name=domainapplication&field_name=investigator"
+            )
+            user_admin = MyUserAdmin(User, self.site)
+            user_queryset = user_admin.get_search_results(user_request, application_queryset, None)[0]
+            current_dropdown = list(user_queryset)
 
             self.assertEqual(expected_dropdown, current_dropdown)
 
@@ -1248,7 +1432,13 @@ class TestDomainApplicationAdmin(MockEppLib):
             self.client.login(username="staffuser", password=p)
             request = RequestFactory().get("/")
 
-            expected_list = list(User.objects.filter(is_staff=True).order_by("first_name", "last_name", "email"))
+            # These names have metadata embedded in them. :investigator implicitly tests if
+            # these are actually from the attribute "investigator".
+            expected_list = [
+                "AGuy AGuy last_name:investigator",
+                "FinalGuy FinalGuy last_name:investigator",
+                "SomeGuy first_name:investigator SomeGuy last_name:investigator",
+            ]
 
             # Get the actual sorted list of investigators from the lookups method
             actual_list = [item for _, item in self.admin.InvestigatorFilter.lookups(self, request, self.admin)]
@@ -1679,12 +1869,47 @@ class AuditedAdminTest(TestCase):
 
         return ordered_list
 
+    def test_alphabetically_sorted_domain_application_investigator(self):
+        """Tests if the investigator field is alphabetically sorted by mimicking
+        the call event flow"""
+        # Creates multiple domain applications - review status does not matter
+        applications = multiple_unalphabetical_domain_objects("application")
+
+        # Create a mock request
+        application_request = self.factory.post(
+            "/admin/registrar/domainapplication/{}/change/".format(applications[0].pk)
+        )
+
+        # Get the formfield data from the application page
+        application_admin = AuditedAdmin(DomainApplication, self.site)
+        field = DomainApplication.investigator.field
+        application_queryset = application_admin.formfield_for_foreignkey(field, application_request).queryset
+
+        request = self.factory.post(
+            "/admin/autocomplete/?app_label=registrar&model_name=domainapplication&field_name=investigator"
+        )
+
+        sorted_fields = ["first_name", "last_name", "email"]
+        desired_sort_order = list(User.objects.filter(is_staff=True).order_by(*sorted_fields))
+
+        # Grab the data returned from get search results
+        admin = MyUserAdmin(User, self.site)
+        search_queryset = admin.get_search_results(request, application_queryset, None)[0]
+        current_sort_order = list(search_queryset)
+
+        self.assertEqual(
+            desired_sort_order,
+            current_sort_order,
+            "Investigator is not ordered alphabetically",
+        )
+
+    # This test case should be refactored in general, as it is too overly specific and engineered
     def test_alphabetically_sorted_fk_fields_domain_application(self):
         with less_console_noise():
             tested_fields = [
                 DomainApplication.authorizing_official.field,
                 DomainApplication.submitter.field,
-                DomainApplication.investigator.field,
+                # DomainApplication.investigator.field,
                 DomainApplication.creator.field,
                 DomainApplication.requested_domain.field,
             ]
@@ -1702,12 +1927,13 @@ class AuditedAdminTest(TestCase):
             # but both fields are of a fixed length.
             # For test case purposes, this should be performant.
             for field in tested_fields:
-                isNamefield: bool = field == DomainApplication.requested_domain.field
-                if isNamefield:
-                    sorted_fields = ["name"]
-                else:
-                    sorted_fields = ["first_name", "last_name"]
-                # We want both of these to be lists, as it is richer test wise.
+                with self.subTest(field=field):
+                    isNamefield: bool = field == DomainApplication.requested_domain.field
+                    if isNamefield:
+                        sorted_fields = ["name"]
+                    else:
+                        sorted_fields = ["first_name", "last_name"]
+                    # We want both of these to be lists, as it is richer test wise.
 
                 desired_order = self.order_by_desired_field_helper(model_admin, request, field.name, *sorted_fields)
                 current_sort_order = list(model_admin.formfield_for_foreignkey(field, request).queryset)
@@ -1839,6 +2065,107 @@ class AuditedAdminTest(TestCase):
                     "{} is not ordered alphabetically".format(field.name),
                 )
 
+    def test_alphabetically_sorted_fk_fields_domain_information(self):
+        tested_fields = [
+            DomainInformation.authorizing_official.field,
+            DomainInformation.submitter.field,
+            # DomainInformation.creator.field,
+            (DomainInformation.domain.field, ["name"]),
+            (DomainInformation.domain_application.field, ["requested_domain__name"]),
+        ]
+        # Creates multiple domain applications - review status does not matter
+        applications = multiple_unalphabetical_domain_objects("information")
+
+        # Create a mock request
+        request = self.factory.post("/admin/registrar/domaininformation/{}/change/".format(applications[0].pk))
+
+        model_admin = AuditedAdmin(DomainInformation, self.site)
+
+        sorted_fields = []
+        # Typically we wouldn't want two nested for fields,
+        # but both fields are of a fixed length.
+        # For test case purposes, this should be performant.
+        for field in tested_fields:
+            isOtherOrderfield: bool = isinstance(field, tuple)
+            field_obj = None
+            if isOtherOrderfield:
+                sorted_fields = field[1]
+                field_obj = field[0]
+            else:
+                sorted_fields = ["first_name", "last_name"]
+                field_obj = field
+            # We want both of these to be lists, as it is richer test wise.
+            desired_order = self.order_by_desired_field_helper(model_admin, request, field_obj.name, *sorted_fields)
+            current_sort_order = list(model_admin.formfield_for_foreignkey(field_obj, request).queryset)
+
+            # Conforms to the same object structure as desired_order
+            current_sort_order_coerced_type = []
+
+            # This is necessary as .queryset and get_queryset
+            # return lists of different types/structures.
+            # We need to parse this data and coerce them into the same type.
+            for obj in current_sort_order:
+                last = None
+                if not isOtherOrderfield:
+                    first = obj.first_name
+                    last = obj.last_name
+                elif field_obj == DomainInformation.domain.field:
+                    first = obj.name
+                elif field_obj == DomainInformation.domain_application.field:
+                    first = obj.requested_domain.name
+
+                name_tuple = self.coerced_fk_field_helper(first, last, field_obj.name, ":")
+                if name_tuple is not None:
+                    current_sort_order_coerced_type.append(name_tuple)
+
+            self.assertEqual(
+                desired_order,
+                current_sort_order_coerced_type,
+                "{} is not ordered alphabetically".format(field_obj.name),
+            )
+
+    def test_alphabetically_sorted_fk_fields_domain_invitation(self):
+        tested_fields = [DomainInvitation.domain.field]
+
+        # Creates multiple domain applications - review status does not matter
+        applications = multiple_unalphabetical_domain_objects("invitation")
+
+        # Create a mock request
+        request = self.factory.post("/admin/registrar/domaininvitation/{}/change/".format(applications[0].pk))
+
+        model_admin = AuditedAdmin(DomainInvitation, self.site)
+
+        sorted_fields = []
+        # Typically we wouldn't want two nested for fields,
+        # but both fields are of a fixed length.
+        # For test case purposes, this should be performant.
+        for field in tested_fields:
+            sorted_fields = ["name"]
+            # We want both of these to be lists, as it is richer test wise.
+
+            desired_order = self.order_by_desired_field_helper(model_admin, request, field.name, *sorted_fields)
+            current_sort_order = list(model_admin.formfield_for_foreignkey(field, request).queryset)
+
+            # Conforms to the same object structure as desired_order
+            current_sort_order_coerced_type = []
+
+            # This is necessary as .queryset and get_queryset
+            # return lists of different types/structures.
+            # We need to parse this data and coerce them into the same type.
+            for contact in current_sort_order:
+                first = contact.name
+                last = None
+
+                name_tuple = self.coerced_fk_field_helper(first, last, field.name, ":")
+                if name_tuple is not None:
+                    current_sort_order_coerced_type.append(name_tuple)
+
+            self.assertEqual(
+                desired_order,
+                current_sort_order_coerced_type,
+                "{} is not ordered alphabetically".format(field.name),
+            )
+
     def coerced_fk_field_helper(self, first_name, last_name, field_name, queryset_shorthand):
         """Handles edge cases for test cases"""
         if first_name is None:
diff --git a/src/registrar/tests/test_reports.py b/src/registrar/tests/test_reports.py
index 630904218..011c60b93 100644
--- a/src/registrar/tests/test_reports.py
+++ b/src/registrar/tests/test_reports.py
@@ -7,13 +7,14 @@ from registrar.models.domain import Domain
 from registrar.models.public_contact import PublicContact
 from registrar.models.user import User
 from django.contrib.auth import get_user_model
+from registrar.models.user_domain_role import UserDomainRole
 from registrar.tests.common import MockEppLib
 from registrar.utility.csv_export import (
-    write_header,
-    write_body,
+    write_csv,
     get_default_start_date,
     get_default_end_date,
 )
+
 from django.core.management import call_command
 from unittest.mock import MagicMock, call, mock_open, patch
 from api.views import get_current_federal, get_current_full
@@ -336,11 +337,30 @@ class ExportDataTest(MockEppLib):
             federal_agency="Armed Forces Retirement Home",
         )
 
+        meoward_user = get_user_model().objects.create(
+            username="meoward_username", first_name="first_meoward", last_name="last_meoward", email="meoward@rocks.com"
+        )
+
+        # Test for more than 1 domain manager
+        _, created = UserDomainRole.objects.get_or_create(
+            user=meoward_user, domain=self.domain_1, role=UserDomainRole.Roles.MANAGER
+        )
+
+        _, created = UserDomainRole.objects.get_or_create(
+            user=self.user, domain=self.domain_1, role=UserDomainRole.Roles.MANAGER
+        )
+
+        # Test for just 1 domain manager
+        _, created = UserDomainRole.objects.get_or_create(
+            user=meoward_user, domain=self.domain_2, role=UserDomainRole.Roles.MANAGER
+        )
+
     def tearDown(self):
         PublicContact.objects.all().delete()
         Domain.objects.all().delete()
         DomainInformation.objects.all().delete()
         User.objects.all().delete()
+        UserDomainRole.objects.all().delete()
         super().tearDown()
 
     def test_export_domains_to_writer_security_emails(self):
@@ -383,8 +403,10 @@ class ExportDataTest(MockEppLib):
             }
             self.maxDiff = None
             # Call the export functions
-            write_header(writer, columns)
-            write_body(writer, columns, sort_fields, filter_condition)
+            write_csv(
+                writer, columns, sort_fields, filter_condition, get_domain_managers=False, should_write_header=True
+            )
+
             # Reset the CSV file's position to the beginning
             csv_file.seek(0)
             # Read the content into a variable
@@ -405,7 +427,7 @@ class ExportDataTest(MockEppLib):
             expected_content = expected_content.replace(",,", "").replace(",", "").replace(" ", "").strip()
             self.assertEqual(csv_content, expected_content)
 
-    def test_write_body(self):
+    def test_write_csv(self):
         """Test that write_body returns the
         existing domain, test that sort by domain name works,
         test that filter works"""
@@ -440,8 +462,9 @@ class ExportDataTest(MockEppLib):
                 ],
             }
             # Call the export functions
-            write_header(writer, columns)
-            write_body(writer, columns, sort_fields, filter_condition)
+            write_csv(
+                writer, columns, sort_fields, filter_condition, get_domain_managers=False, should_write_header=True
+            )
             # Reset the CSV file's position to the beginning
             csv_file.seek(0)
             # Read the content into a variable
@@ -489,8 +512,9 @@ class ExportDataTest(MockEppLib):
                 ],
             }
             # Call the export functions
-            write_header(writer, columns)
-            write_body(writer, columns, sort_fields, filter_condition)
+            write_csv(
+                writer, columns, sort_fields, filter_condition, get_domain_managers=False, should_write_header=True
+            )
             # Reset the CSV file's position to the beginning
             csv_file.seek(0)
             # Read the content into a variable
@@ -567,20 +591,22 @@ class ExportDataTest(MockEppLib):
             }
 
             # Call the export functions
-            write_header(writer, columns)
-            write_body(
+            write_csv(
                 writer,
                 columns,
                 sort_fields,
                 filter_condition,
+                get_domain_managers=False,
+                should_write_header=True,
             )
-            write_body(
+            write_csv(
                 writer,
                 columns,
                 sort_fields_for_deleted_domains,
                 filter_conditions_for_deleted_domains,
+                get_domain_managers=False,
+                should_write_header=False,
             )
-
             # Reset the CSV file's position to the beginning
             csv_file.seek(0)
 
@@ -606,6 +632,64 @@ class ExportDataTest(MockEppLib):
 
             self.assertEqual(csv_content, expected_content)
 
+    def test_export_domains_to_writer_domain_managers(self):
+        """Test that export_domains_to_writer returns the
+        expected domain managers"""
+        with less_console_noise():
+            # Create a CSV file in memory
+            csv_file = StringIO()
+            writer = csv.writer(csv_file)
+            # Define columns, sort fields, and filter condition
+
+            columns = [
+                "Domain name",
+                "Status",
+                "Expiration date",
+                "Domain type",
+                "Agency",
+                "Organization name",
+                "City",
+                "State",
+                "AO",
+                "AO email",
+                "Security contact email",
+            ]
+            sort_fields = ["domain__name"]
+            filter_condition = {
+                "domain__state__in": [
+                    Domain.State.READY,
+                    Domain.State.DNS_NEEDED,
+                    Domain.State.ON_HOLD,
+                ],
+            }
+            self.maxDiff = None
+            # Call the export functions
+            write_csv(
+                writer, columns, sort_fields, filter_condition, get_domain_managers=True, should_write_header=True
+            )
+
+            # Reset the CSV file's position to the beginning
+            csv_file.seek(0)
+            # Read the content into a variable
+            csv_content = csv_file.read()
+            # We expect READY domains,
+            # sorted alphabetially by domain name
+            expected_content = (
+                "Domain name,Status,Expiration date,Domain type,Agency,"
+                "Organization name,City,State,AO,AO email,"
+                "Security contact email,Domain manager email 1,Domain manager email 2,\n"
+                "adomain10.gov,Ready,,Federal,Armed Forces Retirement Home,,,, , ,\n"
+                "adomain2.gov,Dns needed,,Interstate,,,,, , , ,meoward@rocks.com\n"
+                "cdomain1.gov,Ready,,Federal - Executive,World War I Centennial Commission,,,"
+                ", , , ,meoward@rocks.com,info@example.com\n"
+                "ddomain3.gov,On hold,,Federal,Armed Forces Retirement Home,,,, , , ,,\n"
+            )
+            # Normalize line endings and remove commas,
+            # spaces and leading/trailing whitespace
+            csv_content = csv_content.replace(",,", "").replace(",", "").replace(" ", "").replace("\r\n", "\n").strip()
+            expected_content = expected_content.replace(",,", "").replace(",", "").replace(" ", "").strip()
+            self.assertEqual(csv_content, expected_content)
+
 
 class HelperFunctions(TestCase):
     """This asserts that 1=1. Its limited usefulness lies in making sure the helper methods stay healthy."""
diff --git a/src/registrar/utility/csv_export.py b/src/registrar/utility/csv_export.py
index a188fb91c..90e80f551 100644
--- a/src/registrar/utility/csv_export.py
+++ b/src/registrar/utility/csv_export.py
@@ -17,8 +17,9 @@ logger = logging.getLogger(__name__)
 def write_header(writer, columns):
     """
     Receives params from the parent methods and outputs a CSV with a header row.
-    Works with write_header as longas the same writer object is passed.
+    Works with write_header as long as the same writer object is passed.
     """
+
     writer.writerow(columns)
 
 
@@ -43,7 +44,7 @@ def get_domain_infos(filter_condition, sort_fields):
     return domain_infos_cleaned
 
 
-def parse_row(columns, domain_info: DomainInformation, security_emails_dict=None):
+def parse_row(columns, domain_info: DomainInformation, security_emails_dict=None, get_domain_managers=False):
     """Given a set of columns, generate a new row from cleaned column data"""
 
     # Domain should never be none when parsing this information
@@ -77,6 +78,8 @@ def parse_row(columns, domain_info: DomainInformation, security_emails_dict=None
     # create a dictionary of fields which can be included in output
     FIELDS = {
         "Domain name": domain.name,
+        "Status": domain.get_state_display(),
+        "Expiration date": domain.expiration_date,
         "Domain type": domain_type,
         "Agency": domain_info.federal_agency,
         "Organization name": domain_info.organization_name,
@@ -85,39 +88,27 @@ def parse_row(columns, domain_info: DomainInformation, security_emails_dict=None
         "AO": domain_info.ao,  # type: ignore
         "AO email": domain_info.authorizing_official.email if domain_info.authorizing_official else " ",
         "Security contact email": security_email,
-        "Status": domain.get_state_display(),
-        "Expiration date": domain.expiration_date,
         "Created at": domain.created_at,
         "First ready": domain.first_ready,
         "Deleted": domain.deleted,
     }
 
-    # user_emails = [user.email for user in domain.permissions]
+    if get_domain_managers:
+        # Get each domain managers email and add to list
+        dm_emails = [dm.user.email for dm in domain.permissions.all()]
 
-    # Dynamically add user emails to the FIELDS dictionary
-    # for i, user_email in enumerate(user_emails, start=1):
-    #   FIELDS[f"User{i} email"] = user_email
+        # Set up the "matching header" + row field data
+        for i, dm_email in enumerate(dm_emails, start=1):
+            FIELDS[f"Domain manager email {i}"] = dm_email
 
     row = [FIELDS.get(column, "") for column in columns]
     return row
 
 
-def write_body(
-    writer,
-    columns,
-    sort_fields,
-    filter_condition,
-):
+def _get_security_emails(sec_contact_ids):
     """
-    Receives params from the parent methods and outputs a CSV with fltered and sorted domains.
-    Works with write_header as longas the same writer object is passed.
+    Retrieve security contact emails for the given security contact IDs.
     """
-
-    # Get the domainInfos
-    all_domain_infos = get_domain_infos(filter_condition, sort_fields)
-
-    # Store all security emails to avoid epp calls or excessive filters
-    sec_contact_ids = all_domain_infos.values_list("domain__security_contact_registry_id", flat=True)
     security_emails_dict = {}
     public_contacts = (
         PublicContact.objects.only("email", "domain__name")
@@ -133,24 +124,55 @@ def write_body(
         else:
             logger.warning("csv_export -> Domain was none for PublicContact")
 
-    # all_user_nums = 0
-    # for domain_info in all_domain_infos:
-    #     user_num = len(domain_info.domain.permissions)
-    #     all_user_nums.append(user_num)
+    return security_emails_dict
 
-    #     if user_num > highest_user_nums:
-    #         highest_user_nums = user_num
 
-    # Build the header here passing to it highest_user_nums
+def update_columns_with_domain_managers(columns, max_dm_count):
+    """
+    Update the columns list to include "Domain manager email {#}" headers
+    based on the maximum domain manager count.
+    """
+    for i in range(1, max_dm_count + 1):
+        columns.append(f"Domain manager email {i}")
+
+
+def write_csv(
+    writer,
+    columns,
+    sort_fields,
+    filter_condition,
+    get_domain_managers=False,
+    should_write_header=True,
+):
+    """
+    Receives params from the parent methods and outputs a CSV with fltered and sorted domains.
+    Works with write_header as longas the same writer object is passed.
+    get_domain_managers: Conditional bc we only use domain manager info for export_data_full_to_csv
+    should_write_header: Conditional bc export_data_growth_to_csv calls write_body twice
+    """
+
+    all_domain_infos = get_domain_infos(filter_condition, sort_fields)
+
+    # Store all security emails to avoid epp calls or excessive filters
+    sec_contact_ids = all_domain_infos.values_list("domain__security_contact_registry_id", flat=True)
+
+    security_emails_dict = _get_security_emails(sec_contact_ids)
 
     # Reduce the memory overhead when performing the write operation
     paginator = Paginator(all_domain_infos, 1000)
+
+    if get_domain_managers and len(all_domain_infos) > 0:
+        # We want to get the max amont of domain managers an
+        # account has to set the column header dynamically
+        max_dm_count = max(len(domain_info.domain.permissions.all()) for domain_info in all_domain_infos)
+        update_columns_with_domain_managers(columns, max_dm_count)
+
     for page_num in paginator.page_range:
         page = paginator.page(page_num)
         rows = []
         for domain_info in page.object_list:
             try:
-                row = parse_row(columns, domain_info, security_emails_dict)
+                row = parse_row(columns, domain_info, security_emails_dict, get_domain_managers)
                 rows.append(row)
             except ValueError:
                 # This should not happen. If it does, just skip this row.
@@ -158,7 +180,10 @@ def write_body(
                 logger.error("csv_export -> Error when parsing row, domain was None")
                 continue
 
-        writer.writerows(rows)
+    if should_write_header:
+        write_header(writer, columns)
+
+    writer.writerows(rows)
 
 
 def export_data_type_to_csv(csv_file):
@@ -168,6 +193,8 @@ def export_data_type_to_csv(csv_file):
     # define columns to include in export
     columns = [
         "Domain name",
+        "Status",
+        "Expiration date",
         "Domain type",
         "Agency",
         "Organization name",
@@ -176,9 +203,9 @@ def export_data_type_to_csv(csv_file):
         "AO",
         "AO email",
         "Security contact email",
-        "Status",
-        "Expiration date",
+        # For domain manager we are pass it in as a parameter below in write_body
     ]
+
     # Coalesce is used to replace federal_type of None with ZZZZZ
     sort_fields = [
         "organization_type",
@@ -193,8 +220,7 @@ def export_data_type_to_csv(csv_file):
             Domain.State.ON_HOLD,
         ],
     }
-    write_header(writer, columns)
-    write_body(writer, columns, sort_fields, filter_condition)
+    write_csv(writer, columns, sort_fields, filter_condition, get_domain_managers=True, should_write_header=True)
 
 
 def export_data_full_to_csv(csv_file):
@@ -225,8 +251,7 @@ def export_data_full_to_csv(csv_file):
             Domain.State.ON_HOLD,
         ],
     }
-    write_header(writer, columns)
-    write_body(writer, columns, sort_fields, filter_condition)
+    write_csv(writer, columns, sort_fields, filter_condition, get_domain_managers=False, should_write_header=True)
 
 
 def export_data_federal_to_csv(csv_file):
@@ -258,8 +283,7 @@ def export_data_federal_to_csv(csv_file):
             Domain.State.ON_HOLD,
         ],
     }
-    write_header(writer, columns)
-    write_body(writer, columns, sort_fields, filter_condition)
+    write_csv(writer, columns, sort_fields, filter_condition, get_domain_managers=False, should_write_header=True)
 
 
 def get_default_start_date():
@@ -326,6 +350,12 @@ def export_data_growth_to_csv(csv_file, start_date, end_date):
         "domain__deleted__gte": start_date_formatted,
     }
 
-    write_header(writer, columns)
-    write_body(writer, columns, sort_fields, filter_condition)
-    write_body(writer, columns, sort_fields_for_deleted_domains, filter_condition_for_deleted_domains)
+    write_csv(writer, columns, sort_fields, filter_condition, get_domain_managers=False, should_write_header=True)
+    write_csv(
+        writer,
+        columns,
+        sort_fields_for_deleted_domains,
+        filter_condition_for_deleted_domains,
+        get_domain_managers=False,
+        should_write_header=False,
+    )