diff --git a/app/controllers/short_url_requests_controller.rb b/app/controllers/short_url_requests_controller.rb
index b57461ad..942bae7c 100644
--- a/app/controllers/short_url_requests_controller.rb
+++ b/app/controllers/short_url_requests_controller.rb
@@ -64,7 +64,10 @@ def update
         flash[:success] = "Your edit was successful."
         redirect_to short_url_request_path(@short_url_request)
       },
-      failure: -> { render "edit" },
+      failure: lambda {
+        # flash[:alert] = "Bah humbug."
+        render "edit"
+      },
     )
   end
 
diff --git a/spec/controllers/short_url_requests_controller_spec.rb b/spec/controllers/short_url_requests_controller_spec.rb
index fb0c9924..b9c3ad4d 100644
--- a/spec/controllers/short_url_requests_controller_spec.rb
+++ b/spec/controllers/short_url_requests_controller_spec.rb
@@ -314,17 +314,16 @@
   describe "#update" do
     let!(:organisation) { create(:organisation) }
     let!(:short_url_request) { create(:short_url_request, from_path: "/original") }
+    let(:params) do
+      {
+        from_path: short_url_request.from_path,
+        to_path: "/somewhere/different",
+        reason: "Because wombles",
+        organisation_slug: organisation.slug,
+      }
+    end
 
     context "with valid parameters" do
-      let(:params) do
-        {
-          from_path: short_url_request.from_path,
-          to_path: "/somewhere/different",
-          reason: "Because wombles",
-          organisation_slug: organisation.slug,
-        }
-      end
-
       it "saves the changes" do
         put :update, params: { id: short_url_request.id, short_url_request: params }
         expect(response).to redirect_to(short_url_request_path(short_url_request))
@@ -334,6 +333,27 @@
       end
     end
 
+    context "route exists on publishing api already, and override has not been set to yes" do
+      before do
+        stub_request(:any, /#{Plek.find("publishing-api")}\/.*/)
+          .to_return(
+            body: {
+              error: {
+                code: 422,
+                message: "Base path /foo is already reserved by content-tagger",
+              },
+            }.to_json,
+            status: 422,
+          )
+      end
+
+      it "should have a custom flash message" do
+        put :update, params: { id: short_url_request.id, short_url_request: params }
+
+        expect(flash).to eq("foo")
+      end
+    end
+
     context "with a change to the from_path" do
       let(:params) do
         {
diff --git a/spec/features/short_url_manager_responds_to_furl_requests_spec.rb b/spec/features/short_url_manager_responds_to_furl_requests_spec.rb
index bbc3e22b..326e087d 100644
--- a/spec/features/short_url_manager_responds_to_furl_requests_spec.rb
+++ b/spec/features/short_url_manager_responds_to_furl_requests_spec.rb
@@ -141,4 +141,46 @@
       end
     end
   end
+
+  describe "Approving a short URL request when there are complications in Publishing API" do
+    context "Publishing API is down" do
+      before { stub_publishing_api_isnt_available }
+
+      it "shows error message to user" do
+        visit short_url_requests_path
+
+        click_on "Ministry of Beards"
+        click_on "Accept and create redirect"
+        within(".form-errors") do
+          expect(page).to have_content "An error posting to the publishing API prevented this redirect from being created:"
+        end
+      end
+    end
+
+    context "The route is owned by another application" do
+      before do
+        stub_request(:any, /#{Plek.find("publishing-api")}\/.*/)
+          .to_return(
+            body: {
+              error: {
+                code: 422,
+                message: "Base path /foo is already reserved by content-tagger",
+              },
+            }.to_json,
+            status: 422,
+          )
+      end
+
+      it "shows error message to user" do
+        visit short_url_requests_path
+
+        click_on "Ministry of Beards"
+        click_on "Accept and create redirect"
+        within(".form-errors") do
+          expect(page).to have_content "An error posting to the publishing API prevented this redirect from being created:"
+          expect(page).to have_content "Base path /foo is already reserved by content-tagger"
+        end
+      end
+    end
+  end
 end