diff --git a/app/assets/javascripts/pretty-text/addon/emoji/version.js b/app/assets/javascripts/pretty-text/addon/emoji/version.js
index a57796bd774..5b50dd5dec7 100644
--- a/app/assets/javascripts/pretty-text/addon/emoji/version.js
+++ b/app/assets/javascripts/pretty-text/addon/emoji/version.js
@@ -1,4 +1,4 @@
 // DO NOT EDIT THIS FILE!!!
 // Update it by running `rake javascript:update_constants`
 
-export const IMAGE_VERSION = "9";
+export const IMAGE_VERSION = "10";
diff --git a/app/models/emoji.rb b/app/models/emoji.rb
index f755a7eaadf..d9f8c06d19a 100644
--- a/app/models/emoji.rb
+++ b/app/models/emoji.rb
@@ -2,7 +2,7 @@
 
 class Emoji
   # update this to clear the cache
-  EMOJI_VERSION = "9"
+  EMOJI_VERSION = "10"
 
   FITZPATRICK_SCALE ||= [ "1f3fb", "1f3fc", "1f3fd", "1f3fe", "1f3ff" ]
 
diff --git a/plugins/poll/spec/lib/pretty_text_spec.rb b/plugins/poll/spec/lib/pretty_text_spec.rb
index 52fed2284ea..5770f804f3f 100644
--- a/plugins/poll/spec/lib/pretty_text_spec.rb
+++ b/plugins/poll/spec/lib/pretty_text_spec.rb
@@ -165,7 +165,7 @@ describe PrettyText do
     MD
 
     expect(cooked).to include(<<~HTML)
-      <div class="poll-title">What’s your favorite <em>berry</em>? <img src="/images/emoji/twitter/wink.png?v=9" title=":wink:" class="emoji" alt=":wink:"> <a href="https://google.com/" rel="noopener nofollow ugc">https://google.com/</a>
+      <div class="poll-title">What’s your favorite <em>berry</em>? <img src="/images/emoji/twitter/wink.png?v=#{Emoji::EMOJI_VERSION}" title=":wink:" class="emoji" alt=":wink:"> <a href="https://google.com/" rel="noopener nofollow ugc">https://google.com/</a>
       </div>
     HTML
   end
@@ -185,7 +185,7 @@ describe PrettyText do
     MD
 
     expect(cooked).to include(<<~HTML)
-      <div class="poll-title">What’s your favorite <em>berry</em>? <img src="/images/emoji/twitter/wink.png?v=9" title=":wink:" class="emoji" alt=":wink:"> <a href="https://google.com/" rel="noopener nofollow ugc">https://google.com/</a>
+      <div class="poll-title">What’s your favorite <em>berry</em>? <img src="/images/emoji/twitter/wink.png?v=#{Emoji::EMOJI_VERSION}" title=":wink:" class="emoji" alt=":wink:"> <a href="https://google.com/" rel="noopener nofollow ugc">https://google.com/</a>
       </div>
     HTML
 
diff --git a/public/images/emoji/apple/frowning_face_with_open_mouth.png b/public/images/emoji/apple/frowning_face_with_open_mouth.png
new file mode 100644
index 00000000000..e7ef74d9b3c
Binary files /dev/null and b/public/images/emoji/apple/frowning_face_with_open_mouth.png differ
diff --git a/spec/components/pretty_text_spec.rb b/spec/components/pretty_text_spec.rb
index c2e5a611a54..cf9a2145c01 100644
--- a/spec/components/pretty_text_spec.rb
+++ b/spec/components/pretty_text_spec.rb
@@ -159,13 +159,13 @@ describe PrettyText do
 
           html = <<~HTML
             <blockquote>
-            <p>This is a quote with a regular emoji <img src="https://emoji.cdn.com/twitter/upside_down_face.png?v=9" title=":upside_down_face:" class="emoji" alt=":upside_down_face:"></p>
+            <p>This is a quote with a regular emoji <img src="https://emoji.cdn.com/twitter/upside_down_face.png?v=#{Emoji::EMOJI_VERSION}" title=":upside_down_face:" class="emoji" alt=":upside_down_face:"></p>
             </blockquote>
             <blockquote>
-            <p>This is a quote with an emoji shortcut <img src="https://emoji.cdn.com/twitter/slight_smile.png?v=9" title=":slight_smile:" class="emoji" alt=":slight_smile:"></p>
+            <p>This is a quote with an emoji shortcut <img src="https://emoji.cdn.com/twitter/slight_smile.png?v=#{Emoji::EMOJI_VERSION}" title=":slight_smile:" class="emoji" alt=":slight_smile:"></p>
             </blockquote>
             <blockquote>
-            <p>This is a quote with a Unicode emoji <img src="https://emoji.cdn.com/twitter/sunglasses.png?v=9" title=":sunglasses:" class="emoji" alt=":sunglasses:"></p>
+            <p>This is a quote with a Unicode emoji <img src="https://emoji.cdn.com/twitter/sunglasses.png?v=#{Emoji::EMOJI_VERSION}" title=":sunglasses:" class="emoji" alt=":sunglasses:"></p>
             </blockquote>
           HTML
 
@@ -180,13 +180,13 @@ describe PrettyText do
 
           html = <<~HTML
             <blockquote>
-            <p>This is a quote with a regular emoji <img src="https://emoji.cdn.com/twitter/upside_down_face.png?v=9" title=":upside_down_face:" class="emoji" alt=":upside_down_face:"></p>
+            <p>This is a quote with a regular emoji <img src="https://emoji.cdn.com/twitter/upside_down_face.png?v=#{Emoji::EMOJI_VERSION}" title=":upside_down_face:" class="emoji" alt=":upside_down_face:"></p>
             </blockquote>
             <blockquote>
-            <p>This is a quote with an emoji shortcut <img src="https://emoji.cdn.com/twitter/slight_smile.png?v=9" title=":slight_smile:" class="emoji" alt=":slight_smile:"></p>
+            <p>This is a quote with an emoji shortcut <img src="https://emoji.cdn.com/twitter/slight_smile.png?v=#{Emoji::EMOJI_VERSION}" title=":slight_smile:" class="emoji" alt=":slight_smile:"></p>
             </blockquote>
             <blockquote>
-            <p>This is a quote with a Unicode emoji <img src="https://emoji.cdn.com/twitter/sunglasses.png?v=9" title=":sunglasses:" class="emoji" alt=":sunglasses:"></p>
+            <p>This is a quote with a Unicode emoji <img src="https://emoji.cdn.com/twitter/sunglasses.png?v=#{Emoji::EMOJI_VERSION}" title=":sunglasses:" class="emoji" alt=":sunglasses:"></p>
             </blockquote>
           HTML
 
@@ -680,7 +680,7 @@ describe PrettyText do
     context "emojis" do
       it "should remove broken emoji" do
         html = <<~EOS
-          <img src=\"//localhost:3000/images/emoji/twitter/bike.png?v=9\" title=\":bike:\" class=\"emoji\" alt=\":bike:\"> <img src=\"//localhost:3000/images/emoji/twitter/cat.png?v=9\" title=\":cat:\" class=\"emoji\" alt=\":cat:\"> <img src=\"//localhost:3000/images/emoji/twitter/discourse.png?v=9\" title=\":discourse:\" class=\"emoji\" alt=\":discourse:\">
+          <img src=\"//localhost:3000/images/emoji/twitter/bike.png?v=#{Emoji::EMOJI_VERSION}\" title=\":bike:\" class=\"emoji\" alt=\":bike:\"> <img src=\"//localhost:3000/images/emoji/twitter/cat.png?v=#{Emoji::EMOJI_VERSION}\" title=\":cat:\" class=\"emoji\" alt=\":cat:\"> <img src=\"//localhost:3000/images/emoji/twitter/discourse.png?v=#{Emoji::EMOJI_VERSION}\" title=\":discourse:\" class=\"emoji\" alt=\":discourse:\">
         EOS
         expect(PrettyText.excerpt(html, 7)).to eq(":bike: &hellip;")
         expect(PrettyText.excerpt(html, 8)).to eq(":bike: &hellip;")
diff --git a/spec/lib/upload_security_spec.rb b/spec/lib/upload_security_spec.rb
index 32ed9ead8f8..4b5cac79049 100644
--- a/spec/lib/upload_security_spec.rb
+++ b/spec/lib/upload_security_spec.rb
@@ -120,7 +120,7 @@ RSpec.describe UploadSecurity do
 
         describe "when it is based on a regular emoji" do
           it "returns false" do
-            falafel = Emoji.all.find { |e| e.url == '/images/emoji/twitter/falafel.png?v=9' }
+            falafel = Emoji.all.find { |e| e.url == "/images/emoji/twitter/falafel.png?v=#{Emoji::EMOJI_VERSION}" }
             upload.update!(origin: "http://localhost:3000#{falafel.url}")
             expect(subject.should_be_secure?).to eq(false)
           end
diff --git a/spec/models/upload_spec.rb b/spec/models/upload_spec.rb
index c614b28f5d1..b4ad89a66f3 100644
--- a/spec/models/upload_spec.rb
+++ b/spec/models/upload_spec.rb
@@ -466,7 +466,7 @@ describe Upload do
 
       it 'does not mark an upload whose origin matches a regular emoji as secure (sometimes emojis are downloaded in pull_hotlinked_images)' do
         SiteSetting.login_required = true
-        falafel = Emoji.all.find { |e| e.url == '/images/emoji/twitter/falafel.png?v=9' }
+        falafel = Emoji.all.find { |e| e.url == "/images/emoji/twitter/falafel.png?v=#{Emoji::EMOJI_VERSION}" }
         upload.update!(secure: false, origin: "http://localhost:3000#{falafel.url}")
         upload.update_secure_status
         expect(upload.reload.secure).to eq(false)