diff --git a/app/site_files.rb b/app/site_files.rb
index ef0b8bb2..fa429c50 100644
--- a/app/site_files.rb
+++ b/app/site_files.rb
@@ -130,7 +130,9 @@ post '/site_files/upload' do
       end
     end
 
-    file[:filename] = "#{dir_name.force_encoding('UTF-8')}/#{site.scrubbed_path file[:filename].force_encoding('UTF-8')}"
+    file_base_name = site.scrubbed_path file[:filename].force_encoding('UTF-8')
+
+    file[:filename] = "#{dir_name.force_encoding('UTF-8')}/#{file_base_name}"
 
     if current_site.file_size_too_large? file[:tempfile].size
       file_upload_response "#{Rack::Utils.escape_html file[:filename]} is too large, upload cancelled."
@@ -138,6 +140,12 @@ post '/site_files/upload' do
     if !site.okay_to_upload? file
       file_upload_response %{#{Rack::Utils.escape_html file[:filename]}: file type (or content in file) is only supported by <a href="/supporter">supporter accounts</a>. <a href="/site_files/allowed_types">Why We Do This</a>}
     end
+    if SiteFile.path_too_long? file[:filename]
+      file_upload_response "#{Rack::Utils.escape_html file[:filename]}: path is too long, upload cancelled."
+    end
+    if SiteFile.name_too_long? file_base_name
+      file_upload_response "#{Rack::Utils.escape_html file[:filename]}: file name is too long, upload cancelled."
+    end
   end
 
   uploaded_size = params[:files].collect {|f| f[:tempfile].size}.inject{|sum,x| sum + x }
diff --git a/models/site_file.rb b/models/site_file.rb
index 40876358..52305766 100644
--- a/models/site_file.rb
+++ b/models/site_file.rb
@@ -5,10 +5,22 @@ require 'sanitize'
 class SiteFile < Sequel::Model
   CLASSIFIER_LIMIT = 1_000_000
   CLASSIFIER_WORD_LIMIT = 25
+  FILE_PATH_CHARACTER_LIMIT = 300
+  FILE_NAME_CHARACTER_LIMIT = 100
   unrestrict_primary_key
   plugin :update_primary_key
   many_to_one :site
 
+  def self.path_too_long?(filename)
+    return true if filename.length > FILE_PATH_CHARACTER_LIMIT
+    false
+  end
+
+  def self.name_too_long?(filename)
+    return true if filename.length > FILE_NAME_CHARACTER_LIMIT
+    false
+  end
+
   def before_destroy
     if is_directory
       site.site_files_dataset.where(path: /^#{Regexp.quote path}\//, is_directory: true).all.each do |site_file|
diff --git a/tests/site_file_tests.rb b/tests/site_file_tests.rb
index 1c9b7547..24643d17 100644
--- a/tests/site_file_tests.rb
+++ b/tests/site_file_tests.rb
@@ -270,6 +270,28 @@ describe 'site_files' do
       _(File.exists?(@site.files_path('cache.manifest'))).must_equal true
     end
 
+    it 'fails with filename greater than limit' do
+      file_path = './tests/files' + (0...SiteFile::FILE_NAME_CHARACTER_LIMIT+1).map { ('a'..'z').to_a[rand(26)] }.join + '.html'
+      begin
+        File.open(file_path, "w") do |file|
+          file.write("derp")
+        end
+
+        upload 'files[]' => Rack::Test::UploadedFile.new(file_path, 'text/html')
+        _(last_response.body).must_match /name is too long/i
+      ensure
+        FileUtils.rm file_path
+      end
+    end
+
+    it 'fails with path greater than limit' do
+      upload(
+        'dir' => (("a" * 50 + "/") * (SiteFile::FILE_PATH_CHARACTER_LIMIT / 50 - 1) + "a" * 50),
+        'files[]' => Rack::Test::UploadedFile.new('./tests/files/test.jpg', 'image/jpeg')
+      )
+      _(last_response.body).must_match /path is too long/i
+    end
+
     it 'works with otf fonts' do
       upload 'files[]' => Rack::Test::UploadedFile.new('./tests/files/chunkfive.otf', 'application/vnd.ms-opentype')
       _(File.exists?(@site.files_path('chunkfive.otf'))).must_equal true