diff --git a/src/registrar/forms/domain_request_wizard.py b/src/registrar/forms/domain_request_wizard.py
index 789d4498a..95d1f9a4a 100644
--- a/src/registrar/forms/domain_request_wizard.py
+++ b/src/registrar/forms/domain_request_wizard.py
@@ -647,7 +647,6 @@ class CisaRepresentativeForm(BaseDeletableRegistrarForm):
     cisa_representative_email = forms.EmailField(
         required=True,
         max_length=None,
-        error_messages={"invalid": ("Enter your email address in the required format, like name@example.com.")},
         label="Your representative’s email",
         validators=[
             MaxLengthValidator(
@@ -655,14 +654,17 @@ class CisaRepresentativeForm(BaseDeletableRegistrarForm):
                 message="Response must be less than 320 characters.",
             )
         ],
+        error_messages={
+            "invalid": ("Enter your email address in the required format, like name@example.com."),
+            "required": ("Enter the email address of your CISA regional representative."),
+        },
     )
 
 
 class CisaRepresentativeYesNoForm(BaseYesNoForm):
     """Yes/no toggle for the CISA regions question on additional details"""
 
-    # Note that these can be set as functions/init if you need more fine-grained control
-    form_is_checked = property(lambda self: self.domain_request.has_cisa_representative())  # type: ignore
+    form_is_checked = property(lambda self: self.domain_request.has_cisa_representative)
     field_name = "has_cisa_representative"
 
 
@@ -677,6 +679,12 @@ class AdditionalDetailsForm(BaseDeletableRegistrarForm):
                 message="Response must be less than 2000 characters.",
             )
         ],
+        error_messages={
+            "required":  (
+                "Provide additional details you’d like us to know. "
+                "If you have nothing to add, select “No.”"
+            )
+        },
     )
 
 
@@ -684,7 +692,7 @@ class AdditionalDetailsYesNoForm(BaseYesNoForm):
     """Yes/no toggle for the anything else question on additional details"""
 
     # Note that these can be set as functions/init if you need more fine-grained control.
-    form_is_checked = property(lambda self: self.domain_request.has_anything_else_text())  # type: ignore
+    form_is_checked = property(lambda self: self.domain_request.has_anything_else_text)  # type: ignore
     field_name = "has_anything_else_text"
 
 
diff --git a/src/registrar/forms/utility/wizard_form_helper.py b/src/registrar/forms/utility/wizard_form_helper.py
index 2ae50f908..f15382b44 100644
--- a/src/registrar/forms/utility/wizard_form_helper.py
+++ b/src/registrar/forms/utility/wizard_form_helper.py
@@ -263,6 +263,8 @@ class BaseYesNoForm(RegistrarForm):
             },
         )
 
+        print(f"wjat are the error messages? {choice_field.error_messages}")
+
         return choice_field
 
     def get_initial_value(self):
diff --git a/src/registrar/migrations/0086_domainrequest_has_anything_else_text_and_more.py b/src/registrar/migrations/0086_domainrequest_has_anything_else_text_and_more.py
new file mode 100644
index 000000000..5b1d24711
--- /dev/null
+++ b/src/registrar/migrations/0086_domainrequest_has_anything_else_text_and_more.py
@@ -0,0 +1,27 @@
+# Generated by Django 4.2.10 on 2024-04-18 17:59
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("registrar", "0085_domaininformation_cisa_representative_email_and_more"),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name="domainrequest",
+            name="has_anything_else_text",
+            field=models.BooleanField(
+                blank=True, help_text="Determines if the user has a anything_else or not", null=True
+            ),
+        ),
+        migrations.AddField(
+            model_name="domainrequest",
+            name="has_cisa_representative",
+            field=models.BooleanField(
+                blank=True, help_text="Determines if the user has a representative email or not", null=True
+            ),
+        ),
+    ]
diff --git a/src/registrar/models/domain_request.py b/src/registrar/models/domain_request.py
index 1e8091c44..0b6e9a2b4 100644
--- a/src/registrar/models/domain_request.py
+++ b/src/registrar/models/domain_request.py
@@ -647,6 +647,15 @@ class DomainRequest(TimeStampedModel):
         verbose_name="Additional details",
     )
 
+    # This is a drop-in replacement for a has_anything_else_text() function.
+    # In order to track if the user has clicked the yes/no field (while keeping a none default), we need
+    # a tertiary state. We should not display this in /admin.
+    has_anything_else_text = models.BooleanField(
+        null=True,
+        blank=True,
+        help_text="Determines if the user has a anything_else or not",
+    )
+
     cisa_representative_email = models.EmailField(
         null=True,
         blank=True,
@@ -655,6 +664,15 @@ class DomainRequest(TimeStampedModel):
         max_length=320,
     )
 
+    # This is a drop-in replacement for an has_cisa_representative() function.
+    # In order to track if the user has clicked the yes/no field (while keeping a none default), we need
+    # a tertiary state. We should not display this in /admin.
+    has_cisa_representative = models.BooleanField(
+        null=True,
+        blank=True,
+        help_text="Determines if the user has a representative email or not",
+    )
+
     is_policy_acknowledged = models.BooleanField(
         null=True,
         blank=True,
@@ -707,8 +725,25 @@ class DomainRequest(TimeStampedModel):
     def save(self, *args, **kwargs):
         """Save override for custom properties"""
         self.sync_organization_type()
+        self.sync_yes_no_form_fields()
+
         super().save(*args, **kwargs)
 
+    def sync_yes_no_form_fields(self):
+        """Some yes/no forms use a db field to track whether it was checked or not.
+        We handle that here for def save().
+        """
+        # This check is required to ensure that the form doesn't start out checked
+        if self.has_cisa_representative is not None:
+            self.has_cisa_representative = (
+                self.cisa_representative_email != "" and self.cisa_representative_email is not None
+            )
+        
+        if self.anything_else is not None:
+            self.has_anything_else_text = (
+                self.anything_else != "" and self.anything_else is not None
+            )
+
     def __str__(self):
         try:
             if self.requested_domain and self.requested_domain.name:
@@ -1047,16 +1082,8 @@ class DomainRequest(TimeStampedModel):
         """Does this domain request have other contacts listed?"""
         return self.other_contacts.exists()
 
-    def has_anything_else_text(self) -> bool:
-        """Does this domain request have an 'anything else?' entry"""
-        return self.anything_else != "" and self.anything_else is not None
-
-    def has_cisa_representative(self) -> bool:
-        """Does this domain request have cisa representative?"""
-        return self.cisa_representative_email != "" and self.cisa_representative_email is not None
-
     def has_additional_details(self) -> bool:
-        return self.has_anything_else_text() or self.has_cisa_representative()
+        return self.has_anything_else_text() or self.has_cisa_representative
 
     def is_federal(self) -> Union[bool, None]:
         """Is this domain request for a federal agency?