diff --git a/app/controllers/application_controller.rb b/app/controllers/application_controller.rb
index 6807ba47c..fbc4e86b4 100644
--- a/app/controllers/application_controller.rb
+++ b/app/controllers/application_controller.rb
@@ -22,7 +22,7 @@ def new_session_path(_scope)
     #
     # @return [String] a combined error message for the work and transition error
     #
-    def message_from_assm_error(aasm_error:, work:)
+    def message_from_aasm_error(aasm_error:, work:)
       message = aasm_error.message
       if work.errors.count > 0
         message = work.errors.to_a.join(", ")
@@ -99,7 +99,7 @@ def prepare_decorators_for_work_form(work)
     def rescue_aasm_error
       yield
     rescue AASM::InvalidTransition => error
-      message = message_from_assm_error(aasm_error: error, work: @work)
+      message = message_from_aasm_error(aasm_error: error, work: @work)
 
       Honeybadger.notify("Invalid #{@work.current_transition}: #{error.message} errors: #{message}")
       transition_error_message = "We apologize, the following errors were encountered: #{message}. Please contact the PDC Describe administrators for any assistance."
diff --git a/app/controllers/works_wizard_controller.rb b/app/controllers/works_wizard_controller.rb
index 2d726af18..8956cfd8a 100644
--- a/app/controllers/works_wizard_controller.rb
+++ b/app/controllers/works_wizard_controller.rb
@@ -110,6 +110,7 @@ def review
   # PATCH /works/1/validate-wizard
   def validate
     @work.submission_notes = params["submission_notes"]
+
     if params[:save_only] == "true"
       @work.save
       render :review
@@ -139,11 +140,19 @@ def readme_uploaded
     end
   end
 
+  def files_param
+    params["files"]
+  end
+
   # Uploads the README file, called by Uppy.
   # POST /works/1/readme-uploaded-payload
   def readme_uploaded_payload
+    raise StandardError("Only one README file can be uploaded.") if files_param.empty?
+    raise StandardError("Only one README file can be uploaded.") if files_param.length > 1
+
+    readme_file = files_param.first
     readme = Readme.new(@work, current_user)
-    readme_file = params["files"].first
+
     readme_error = readme.attach(readme_file)
     if readme_error.nil?
       render plain: readme.file_name
@@ -158,6 +167,19 @@ def file_location_url
   end
   helper_method :file_location_url
 
+  def rescue_aasm_error
+    yield
+  rescue AASM::InvalidTransition => error
+    message = message_from_aasm_error(aasm_error: error, work: @work)
+
+    Honeybadger.notify("Invalid #{@work.current_transition}: #{error.message} errors: #{message}")
+    transition_error_message = "We apologize, the following errors were encountered: #{message}."
+    @errors = [transition_error_message]
+
+    # redirect_to root_url, notice: transition_error_message
+    redirect_aasm_error(transition_error_message)
+  end
+
   private
 
     def edit_helper(view_name, redirect_url)
@@ -204,7 +226,7 @@ def readme_file_param
       patch_params[:readme_file]
     end
 
-    def rescue_aasm_error
+    def rescue_aasm_error_dis
       super
     rescue StandardError => generic_error
       redirect_to root_url, notice: "We apologize, an error was encountered: #{generic_error.message}. Please contact the PDC Describe administrators."
diff --git a/app/helpers/application_helper.rb b/app/helpers/application_helper.rb
index 89fa07dc3..140b0fef5 100644
--- a/app/helpers/application_helper.rb
+++ b/app/helpers/application_helper.rb
@@ -7,6 +7,13 @@ def html_tag_attributes
     { lang: I18n.locale }
   end
 
+  def flash_notice
+    value = flash[:notice]
+    # rubocop:disable Rails/OutputSafety
+    value.html_safe
+    # rubocop:enable Rails/OutputSafety
+  end
+
   def pre_curation_uploads_file_name(file:)
     value = file.filename.to_s
     return if value.blank?
diff --git a/app/models/work.rb b/app/models/work.rb
index e8fbd0794..31955a3f6 100644
--- a/app/models/work.rb
+++ b/app/models/work.rb
@@ -302,12 +302,26 @@ def current_transition
     aasm.current_event.to_s.humanize.delete("!")
   end
 
+  # Retrieve the S3 file uploads associated with the Work
+  # @return [Array<S3File>]
   def uploads
     return post_curation_uploads if approved?
 
     pre_curation_uploads
   end
 
+  # Retrieve the S3 file uploads named "README"
+  # @return [Array<S3File>]
+  def readme_uploads
+    uploads.select { |s3_file| s3_file.filename.include?("README") }
+  end
+
+  # Retrieve the S3 file uploads which are research artifacts proper (not README or other files providing metadata/documentation)
+  # @return [Array<S3File>]
+  def artifact_uploads
+    uploads.reject { |s3_file| s3_file.filename.include?("README") }
+  end
+
   # Returns the list of files for the work with some basic information about each of them.
   # This method is much faster than `uploads` because it does not return the actual S3File
   # objects to the client, instead it returns just a few selected data elements.
diff --git a/app/services/work_validator.rb b/app/services/work_validator.rb
index 3eaa5216c..d068185e8 100644
--- a/app/services/work_validator.rb
+++ b/app/services/work_validator.rb
@@ -1,5 +1,6 @@
 # frozen_string_literal: true
 class WorkValidator
+  include Rails.application.routes.url_helpers
   attr_reader :work
 
   delegate :errors, :metadata, :resource, :ark, :doi, :user_entered_doi, :id, :group,
@@ -51,7 +52,7 @@ def valid_to_approve(user)
     end
     validate_files
     if pre_curation_uploads.empty? && post_curation_uploads.empty?
-      errors.add :base, "Uploads must be present for a work to be approved"
+      errors.add(:base, "You must include at least one file. <a href='#{work_file_upload_path(work)}'>Please upload one</a>")
     end
     errors.count == 0
   end
@@ -161,6 +162,7 @@ def validate_metadata
     def validate_files
       return if @work.resource.migrated
       readme = Readme.new(work, nil)
-      errors.add(:base, "Must provide a README") if readme.blank?
+      errors.add(:base, "You must include a README. <a href='#{work_readme_select_path(work)}'>Please upload one</a>") if readme.blank?
+      errors.add(:base, "You must provide only one README file upload") if work.readme_uploads.length > 1
     end
 end
diff --git a/app/views/layouts/application.html.erb b/app/views/layouts/application.html.erb
index e6654d71b..a99d49432 100644
--- a/app/views/layouts/application.html.erb
+++ b/app/views/layouts/application.html.erb
@@ -43,7 +43,7 @@
       <% if flash[:notice] %>
         <div class="row">
           <div class="col">
-            <div class="alert alert-warning" role="alert" ><%= flash[:notice] %></div>
+            <div class="alert alert-warning" role="alert" ><%= flash_notice %></div>
           </div>
         </div>
       <% end %>
diff --git a/spec/controllers/works_controller_spec.rb b/spec/controllers/works_controller_spec.rb
index 95c929235..0bf6184d8 100644
--- a/spec/controllers/works_controller_spec.rb
+++ b/spec/controllers/works_controller_spec.rb
@@ -725,15 +725,26 @@
       end
 
       context "no files attached" do
-        it "handles aproval errors" do
-          fake_s3_service = stub_s3 data: [FactoryBot.build(:s3_readme)]
+        let(:data) do
+          [
+            FactoryBot.build(:s3_readme),
+            FactoryBot.build(:s3_file)
+          ]
+        end
+        let(:fake_s3_service) { stub_s3(data:) }
+        before do
+          fake_s3_service
           work.complete_submission!(user)
           allow(fake_s3_service).to receive(:client_s3_files).and_return([])
           sign_in curator
+        end
+        it "handles aproval errors" do
           post :approve, params: { id: work.id }
           expect(response.status).to be 302
           # rubocop:disable Layout/LineLength
-          expect(assigns[:errors]).to eq(["We apologize, the following errors were encountered: Must provide a README, Uploads must be present for a work to be approved. Please contact the PDC Describe administrators for any assistance."])
+          # binding.pry
+          # "We apologize, the following errors were encountered: You must include a README. <a href='/works/1/readme-select'>Please upload one</a>, You must include at least one file. <a href='/works/1/file-upload'>Please upload one</a>. Please contact the PDC Describe administrators for any assistance."
+          expect(assigns[:errors]).to eq(["We apologize, the following errors were encountered: You must include a README. <a href='#{work_readme_select_path(work)}'>Please upload one</a>, You must include at least one file. <a href='#{work_file_upload_path(work)}'>Please upload one</a>. Please contact the PDC Describe administrators for any assistance."])
           # rubocop:enable Layout/LineLength
         end
       end
@@ -1263,7 +1274,9 @@
       sign_in user
       post :validate, params: { id: work.id }
       expect(response).to redirect_to(edit_work_path(work))
-      expect(controller.flash[:notice]).to eq("We apologize, the following errors were encountered: Must provide a README. Please contact the PDC Describe administrators for any assistance.")
+      # rubocop:disable Layout/LineLength
+      expect(controller.flash[:notice]).to eq("We apologize, the following errors were encountered: You must include a README. <a href='#{work_readme_select_path(work)}'>Please upload one</a>. Please contact the PDC Describe administrators for any assistance.")
+      # rubocop:enable Layout/LineLength
     end
 
     it "validates a work completes it when there are no errors" do
diff --git a/spec/controllers/works_wizard_controller_spec.rb b/spec/controllers/works_wizard_controller_spec.rb
index 8c34eb46d..29b92e26e 100644
--- a/spec/controllers/works_wizard_controller_spec.rb
+++ b/spec/controllers/works_wizard_controller_spec.rb
@@ -354,7 +354,7 @@
           expect(response.status).to be 302
           expect(work.reload).to be_draft
           # rubocop:disable Layout/LineLength
-          expect(assigns[:errors]).to eq(["We apologize, the following errors were encountered: Must provide a description. Please contact the PDC Describe administrators for any assistance."])
+          expect(assigns[:errors]).to eq(["We apologize, the following errors were encountered: Must provide a description."])
           # rubocop:enable Layout/LineLength
         end
       end
@@ -368,5 +368,67 @@
         end
       end
     end
+
+    context "a work with multiple README files" do
+      describe "#validate" do
+        before do
+          stub_s3(data: [
+                    FactoryBot.build(:s3_readme),
+                    FactoryBot.build(:s3_readme)
+                  ])
+          sign_in(user)
+        end
+
+        it "renders the error message" do
+          work.save
+          post :validate, params: { id: work.id }
+          expect(response).to redirect_to(edit_work_wizard_path(work))
+          expect(response.status).to be 302
+          expect(work.reload).to be_draft
+          # rubocop:disable Layout/LineLength
+          expect(assigns[:errors]).to eq(["We apologize, the following errors were encountered: You must provide only one README file upload."])
+          # rubocop:enable Layout/LineLength
+        end
+      end
+    end
+
+    context "a work with one README but no uploaded files" do
+      describe "#validate" do
+        before do
+          stub_s3(data: [
+                    FactoryBot.build(:s3_readme)
+                  ])
+          sign_in(user)
+          post :validate, params: { id: work.id }
+          work.reload
+        end
+
+        it "advances the Work from the 'draft' state to the 'awaiting_approval' state" do
+          expect(response).to redirect_to("/works/#{work.id}/complete")
+          expect(response.status).to be 302
+          expect(work.state).to eq("awaiting_approval")
+        end
+      end
+    end
+
+    context "a work with no README files" do
+      describe "#validate" do
+        before do
+          stub_s3(data: [])
+          sign_in(user)
+        end
+
+        it "renders the error message" do
+          work.save
+          post :validate, params: { id: work.id }
+          expect(response).to redirect_to(edit_work_wizard_path(work))
+          expect(response.status).to be 302
+          expect(work.reload).to be_draft
+          # rubocop:disable Layout/LineLength
+          expect(assigns[:errors]).to eq(["We apologize, the following errors were encountered: You must include a README. <a href='#{work_readme_select_path(work)}'>Please upload one</a>."])
+          # rubocop:enable Layout/LineLength
+        end
+      end
+    end
   end
 end
diff --git a/spec/requests/works_spec.rb b/spec/requests/works_spec.rb
index 51806a191..8a0704334 100644
--- a/spec/requests/works_spec.rb
+++ b/spec/requests/works_spec.rb
@@ -309,7 +309,7 @@
 
           expect(response.status).to eq(200)
           # rubocop:disable Layout/LineLength
-          error_message = ERB::Util.html_escape("We apologize, the following errors were encountered: Event 'approve' cannot transition from 'draft'. Please contact the PDC Describe administrators for any assistance.")
+          error_message = "We apologize, the following errors were encountered: Event 'approve' cannot transition from 'draft'. Please contact the PDC Describe administrators for any assistance."
           # rubocop:enable Layout/LineLength
           expect(response.body).to include(error_message)
         end
@@ -328,7 +328,7 @@
 
           expect(response.status).to eq(200)
           # rubocop:disable Layout/LineLength
-          error_message = ERB::Util.html_escape("We apologize, the following errors were encountered: Event 'approve' cannot transition from 'draft'. Please contact the PDC Describe administrators for any assistance.")
+          error_message = "We apologize, the following errors were encountered: Event 'approve' cannot transition from 'draft'. Please contact the PDC Describe administrators for any assistance."
           # rubocop:enable Layout/LineLength
           expect(response.body).to include(error_message)
         end
diff --git a/spec/services/work_validator_spec.rb b/spec/services/work_validator_spec.rb
index 704d4efe3..c0a6db179 100644
--- a/spec/services/work_validator_spec.rb
+++ b/spec/services/work_validator_spec.rb
@@ -69,7 +69,9 @@
       validator = WorkValidator.new(work)
       expect(validator.valid?).to be_truthy # we can still save, we just can not transition to awaiting approval
       expect(validator.valid_to_complete).to be_falsey
-      expect(work.errors.full_messages).to eq(["Must provide a README"])
+      expect(work.errors.full_messages).not_to be_empty
+      full_message = work.errors.full_messages[0]
+      expect(full_message).to eq("You must include a README. <a href='/works/#{work.id}/readme-select'>Please upload one</a>")
     end
 
     context "a migrated work" do
diff --git a/spec/system/migrate_submission_spec.rb b/spec/system/migrate_submission_spec.rb
index c24823ce3..407f2b267 100644
--- a/spec/system/migrate_submission_spec.rb
+++ b/spec/system/migrate_submission_spec.rb
@@ -153,7 +153,7 @@
       fill_in "title_main", with: title
       click_on "Create"
       click_on "Complete"
-      expect(page).to have_content "Must provide a README"
+      expect(page).to have_content "You must include a README."
 
       # fake that the user put a file up in globus
       allow(fake_s3_service).to receive(:client_s3_files).and_return([FactoryBot.build(:s3_readme)])
diff --git a/spec/system/work_approve_spec.rb b/spec/system/work_approve_spec.rb
index 670543871..9fe5c5cb1 100644
--- a/spec/system/work_approve_spec.rb
+++ b/spec/system/work_approve_spec.rb
@@ -19,7 +19,7 @@
       expect(page).to have_content(work.doi)
       click_on "Approve Dataset"
       page.driver.browser.switch_to.alert.accept
-      expect(page).to have_content("Uploads must be present for a work to be approved")
+      expect(page).to have_content("You must include at least one file. Please upload one.")
     end
 
     it "does not display warning if user cancels approval", js: true do
@@ -29,8 +29,9 @@
       click_link work.title
       expect(page).to have_content(work.doi)
       click_on "Approve Dataset"
+      sleep(0.5)
       page.driver.browser.switch_to.alert.dismiss
-      expect(page).to_not have_content("Uploads must be present for a work to be approved")
+      expect(page).not_to have_content("You must include at least one file. Please upload one.")
     end
   end
 end