diff --git a/app/assets/javascripts/discourse/app/components/fast-edit.gjs b/app/assets/javascripts/discourse/app/components/fast-edit.gjs
index c68e8d8e777..d6df5ab7226 100644
--- a/app/assets/javascripts/discourse/app/components/fast-edit.gjs
+++ b/app/assets/javascripts/discourse/app/components/fast-edit.gjs
@@ -53,6 +53,13 @@ export default class FastEdit extends Component {
       const result = await ajax(`/posts/${this.args.post.id}`);
       const newRaw = result.raw.replace(this.args.initialValue, this.value);
 
+      // Warn the user if we failed to update the post
+      if (newRaw === result.raw) {
+        throw new Error(
+          "Failed to update the post. Did your fast edit include a special character?"
+        );
+      }
+
       await this.args.post.save({ raw: newRaw });
     } catch (error) {
       popupAjaxError(error);
diff --git a/app/assets/javascripts/discourse/app/components/post-text-selection.gjs b/app/assets/javascripts/discourse/app/components/post-text-selection.gjs
index f92e55c7f0e..af9a9b51969 100644
--- a/app/assets/javascripts/discourse/app/components/post-text-selection.gjs
+++ b/app/assets/javascripts/discourse/app/components/post-text-selection.gjs
@@ -190,6 +190,7 @@ export default class PostTextSelection extends Component {
         quoteState.buffer.length === 0 ||
         quoteState.buffer.includes("|") || // tables are too complex
         quoteState.buffer.match(/\n/g) || // linebreaks are too complex
+        quoteState.buffer.match(/[‚‘’„“”«»‹›™±…→←↔¶]/g) || // typopgraphic characters are too complex
         matches?.length !== 1 // duplicates are too complex
       ) {
         supportsFastEdit = false;
diff --git a/app/assets/javascripts/discourse/tests/acceptance/fast-edit-test.js b/app/assets/javascripts/discourse/tests/acceptance/fast-edit-test.js
index cd8b91c2b39..43743d16d7f 100644
--- a/app/assets/javascripts/discourse/tests/acceptance/fast-edit-test.js
+++ b/app/assets/javascripts/discourse/tests/acceptance/fast-edit-test.js
@@ -11,9 +11,7 @@ import { cloneJSON } from "discourse-common/lib/object";
 
 acceptance("Fast Edit", function (needs) {
   needs.user();
-  needs.settings({
-    enable_fast_edit: true,
-  });
+  needs.settings({ enable_fast_edit: true });
   needs.pretender((server, helper) => {
     server.get("/posts/419", () => {
       return helper.response(cloneJSON(postFixtures["/posts/398"]));
@@ -86,6 +84,19 @@ acceptance("Fast Edit", function (needs) {
     assert.dom(".d-editor-input").exists();
   });
 
+  test("Opens full composer when selection has typographic characters", async function (assert) {
+    await visit("/t/internationalization-localization/280");
+
+    query("#post_2 .cooked").append(`That’s what she said!`);
+    const textNode = query("#post_2 .cooked").childNodes[2];
+
+    await selectText(textNode);
+    await click(".quote-button .quote-edit-label");
+
+    assert.dom("#fast-edit-input").doesNotExist();
+    assert.dom(".d-editor-input").exists();
+  });
+
   test("Works with diacritics", async function (assert) {
     await visit("/t/internationalization-localization/280");
 
diff --git a/spec/system/post_selection_fast_edit_spec.rb b/spec/system/post_selection_fast_edit_spec.rb
index fe03dd4d8fe..ee6763abc39 100644
--- a/spec/system/post_selection_fast_edit_spec.rb
+++ b/spec/system/post_selection_fast_edit_spec.rb
@@ -3,46 +3,54 @@
 describe "Post selection | Fast edit", type: :system do
   let(:topic_page) { PageObjects::Pages::Topic.new }
   let(:fast_editor) { PageObjects::Components::FastEditor.new }
+
   fab!(:topic)
-  fab!(:post) { Fabricate(:post, topic: topic) }
-  fab!(:post_2) { Fabricate(:post, topic: topic, raw: "It ‘twas a great’ “time”!") }
-  fab!(:spanish_post) { Fabricate(:post, topic: topic, raw: "Hola Juan, ¿cómo estás?") }
-  fab!(:chinese_post) { Fabricate(:post, topic: topic, raw: "这是一个测试") }
-  fab!(:post_with_emoji) { Fabricate(:post, topic: topic, raw: "Good morning :wave:!") }
+
+  fab!(:post) { Fabricate(:post, topic:) }
+  fab!(:post_2) { Fabricate(:post, topic:, raw: "It ‘twas a great’ “time”!") }
+  fab!(:spanish_post) { Fabricate(:post, topic:, raw: "Hola Juan, ¿cómo estás?") }
+  fab!(:chinese_post) { Fabricate(:post, topic:, raw: "这是一个测试") }
+  fab!(:post_with_emoji) { Fabricate(:post, topic:, raw: "Good morning :wave:!") }
   fab!(:post_with_quote) do
     Fabricate(
       :post,
-      topic: topic,
+      topic:,
       raw: "[quote]\n#{post_2.raw}\n[/quote]\n\nBelle journée, n'est-ce pas ?",
     )
   end
+
   fab!(:current_user) { Fabricate(:admin) }
 
   before { sign_in(current_user) }
 
-  context "when text selected it opens contact menu and fast editor" do
-    it "opens context menu and fast edit dialog" do
+  def css(post) = "#{topic_page.post_by_number_selector(post.post_number)} .cooked p"
+
+  context "when text is selected" do
+    before do
       topic_page.visit_topic(topic)
-
-      select_text_range("#{topic_page.post_by_number_selector(1)} .cooked p", 0, 10)
-      expect(topic_page.fast_edit_button).to be_visible
-
-      topic_page.click_fast_edit_button
-      expect(topic_page.fast_edit_input).to be_visible
+      select_text_range(css(post), 0, 5)
     end
 
-    it "edits first paragraph and saves changes" do
-      topic_page.visit_topic(topic)
+    it "opens context menu" do
+      expect(topic_page.fast_edit_button).to be_visible
+    end
 
-      select_text_range("#{topic_page.post_by_number_selector(1)} .cooked p", 0, 5)
-      topic_page.click_fast_edit_button
+    context "when clicking the fast edit button" do
+      before { topic_page.click_fast_edit_button }
 
-      fast_editor.fill_content("Howdy")
-      fast_editor.save
+      it "opens the fast editor" do
+        expect(topic_page.fast_edit_input).to be_visible
+      end
 
-      within("#post_1 .cooked > p") do |el|
-        expect(el).not_to eq("Hello world")
-        expect(el).to have_content("Howdy")
+      context "when entering some text and clicking the save button" do
+        before do
+          fast_editor.fill_content("Howdy")
+          fast_editor.save
+        end
+
+        it "saves changes" do
+          expect(page).to have_selector(css(post), text: "Howdy world")
+        end
       end
     end
   end
@@ -51,7 +59,7 @@ describe "Post selection | Fast edit", type: :system do
     it "opens the composer directly" do
       topic_page.visit_topic(topic)
 
-      select_text_range("#{topic_page.post_by_number_selector(6)} .cooked p", 5, 10)
+      select_text_range(css(post_with_quote), 5, 10)
       topic_page.click_fast_edit_button
 
       expect(topic_page).to have_expanded_composer
@@ -59,63 +67,56 @@ describe "Post selection | Fast edit", type: :system do
   end
 
   context "when editing text that has strange characters" do
-    it "saves when paragraph contains apostrophe" do
+    it "saves when paragraph contains apostrophes" do
       topic_page.visit_topic(topic)
 
-      select_text_range("#{topic_page.post_by_number_selector(2)} .cooked p", 19, 4)
+      select_text_range(css(post_2), 19, 4)
       topic_page.click_fast_edit_button
 
       fast_editor.fill_content("day")
       fast_editor.save
 
-      expect(page).to have_selector(
-        "#{topic_page.post_by_number_selector(2)} .cooked p",
-        text: "It ‘twas a great’ “day”!",
-      )
+      expect(page).to have_selector(css(post_2), text: "It ‘twas a great’ “day”!")
     end
 
-    it "saves when text contains diacratics" do
+    it "saves when text contains diacritics" do
       topic_page.visit_topic(topic)
 
-      select_text_range("#{topic_page.post_by_number_selector(3)} .cooked p", 11, 12)
+      select_text_range(css(spanish_post), 11, 12)
 
       topic_page.click_fast_edit_button
 
       fast_editor.fill_content("¿está todo bien?")
       fast_editor.save
 
-      expect(page).to have_selector(
-        "#{topic_page.post_by_number_selector(3)} .cooked p",
-        text: "Hola Juan, ¿está todo bien?",
-      )
+      expect(page).to have_selector(css(spanish_post), text: "Hola Juan, ¿está todo bien?")
     end
 
     it "saves when text contains CJK ranges" do
       topic_page.visit_topic(topic)
 
-      select_text_range("#{topic_page.post_by_number_selector(4)} .cooked p", 0, 2)
+      select_text_range(css(chinese_post), 0, 2)
       topic_page.click_fast_edit_button
 
       fast_editor.fill_content("今天")
       fast_editor.save
 
-      expect(page).to have_selector(
-        "#{topic_page.post_by_number_selector(4)} .cooked p",
-        text: "今天一个测试",
-      )
+      expect(page).to have_selector(css(chinese_post), text: "今天一个测试")
     end
 
     it "saves when text contains emoji" do
       topic_page.visit_topic(topic)
 
-      select_text_range("#{topic_page.post_by_number_selector(5)} .cooked p", 5, 7)
+      select_text_range(css(post_with_emoji), 5, 7)
       topic_page.click_fast_edit_button
 
       fast_editor.fill_content("day")
       fast_editor.save
 
-      expect(page).to have_no_css("#fast-edit-input")
-      expect(post_with_emoji.raw).to eq("Good day :wave:!")
+      # NOTE: the emoji isn't picked up by the "text:" selector
+      expect(page).to have_selector(css(post_with_emoji), text: "Good day !")
+      # So we also check the raw content to ensure it's been saved correctly
+      expect(post_with_emoji.reload.raw).to eq "Good day :wave:!"
     end
   end
 end