diff --git a/app/assets/javascripts/discourse/app/templates/components/emoji-group-sections.hbs b/app/assets/javascripts/discourse/app/templates/components/emoji-group-sections.hbs
index 581c54d34f..82ada7fe25 100644
--- a/app/assets/javascripts/discourse/app/templates/components/emoji-group-sections.hbs
+++ b/app/assets/javascripts/discourse/app/templates/components/emoji-group-sections.hbs
@@ -8,7 +8,7 @@
   <div class="section-group">
     {{replace-emoji ":grinning:" (hash lazy=true)}}
     {{replace-emoji ":smiley:" (hash lazy=true)}}
-    {{replace-emoji ":smile:" (hash lazy=true)}}
+    {{replace-emoji ":grinning_face_with_smiling_eyes:" (hash lazy=true)}}
     {{replace-emoji ":grin:" (hash lazy=true)}}
     {{replace-emoji ":laughing:" (hash lazy=true)}}
     {{replace-emoji ":sweat_smile:" (hash lazy=true)}}
@@ -78,6 +78,7 @@
     {{replace-emoji ":flushed:" (hash lazy=true)}}
     {{replace-emoji ":pleading_face:" (hash lazy=true)}}
     {{replace-emoji ":frowning:" (hash lazy=true)}}
+    {{replace-emoji ":frowning_face_with_open_mouth:" (hash lazy=true)}}
     {{replace-emoji ":anguished:" (hash lazy=true)}}
     {{replace-emoji ":fearful:" (hash lazy=true)}}
     {{replace-emoji ":cold_sweat:" (hash lazy=true)}}
diff --git a/app/assets/javascripts/pretty-text/addon/emoji.js b/app/assets/javascripts/pretty-text/addon/emoji.js
index 2237fe851d..3ff60de061 100644
--- a/app/assets/javascripts/pretty-text/addon/emoji.js
+++ b/app/assets/javascripts/pretty-text/addon/emoji.js
@@ -21,45 +21,12 @@ export function extendedEmojiList() {
 
 const emojiHash = {};
 
-export function buildReplacementsList(emojiReplacements) {
-  return Object.keys(emojiReplacements)
-    .sort()
-    .reverse()
-    .map((emoji) => {
-      return emoji
-        .split("")
-        .map((chr) => {
-          return "\\u" + chr.charCodeAt(0).toString(16).padStart(4, "0");
-        })
-        .join("");
-    })
-    .join("|");
-}
+// https://github.com/mathiasbynens/emoji-regex/blob/main/text.js
+export const emojiReplacementRegex =
+  "\uD83C\uDFF4\uDB40\uDC67\uDB40\uDC62(?:\uDB40\uDC77\uDB40\uDC6C\uDB40\uDC73|\uDB40\uDC73\uDB40\uDC63\uDB40\uDC74|\uDB40\uDC65\uDB40\uDC6E\uDB40\uDC67)\uDB40\uDC7F|(?:\uD83E\uDDD1\uD83C\uDFFF\u200D\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D)?\uD83E\uDDD1|\uD83D\uDC69\uD83C\uDFFF\u200D\uD83E\uDD1D\u200D(?:\uD83D[\uDC68\uDC69]))(?:\uD83C[\uDFFB-\uDFFE])|(?:\uD83E\uDDD1\uD83C\uDFFE\u200D\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D)?\uD83E\uDDD1|\uD83D\uDC69\uD83C\uDFFE\u200D\uD83E\uDD1D\u200D(?:\uD83D[\uDC68\uDC69]))(?:\uD83C[\uDFFB-\uDFFD\uDFFF])|(?:\uD83E\uDDD1\uD83C\uDFFD\u200D\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D)?\uD83E\uDDD1|\uD83D\uDC69\uD83C\uDFFD\u200D\uD83E\uDD1D\u200D(?:\uD83D[\uDC68\uDC69]))(?:\uD83C[\uDFFB\uDFFC\uDFFE\uDFFF])|(?:\uD83E\uDDD1\uD83C\uDFFC\u200D\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D)?\uD83E\uDDD1|\uD83D\uDC69\uD83C\uDFFC\u200D\uD83E\uDD1D\u200D(?:\uD83D[\uDC68\uDC69]))(?:\uD83C[\uDFFB\uDFFD-\uDFFF])|(?:\uD83E\uDDD1\uD83C\uDFFB\u200D\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D)?\uD83E\uDDD1|\uD83D\uDC69\uD83C\uDFFB\u200D\uD83E\uDD1D\u200D(?:\uD83D[\uDC68\uDC69]))(?:\uD83C[\uDFFC-\uDFFF])|\uD83D\uDC68(?:\uD83C\uDFFB(?:\u200D(?:\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D\uD83D\uDC68(?:\uD83C[\uDFFB-\uDFFF])|\uD83D\uDC68(?:\uD83C[\uDFFB-\uDFFF]))|\uD83E\uDD1D\u200D\uD83D\uDC68(?:\uD83C[\uDFFC-\uDFFF])|[\u2695\u2696\u2708]\uFE0F|\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD]))?|(?:\uD83C[\uDFFC-\uDFFF])\u200D\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D\uD83D\uDC68(?:\uD83C[\uDFFB-\uDFFF])|\uD83D\uDC68(?:\uD83C[\uDFFB-\uDFFF]))|\u200D(?:\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D)?\uD83D\uDC68|(?:\uD83D[\uDC68\uDC69])\u200D(?:\uD83D\uDC66\u200D\uD83D\uDC66|\uD83D\uDC67\u200D(?:\uD83D[\uDC66\uDC67]))|\uD83D\uDC66\u200D\uD83D\uDC66|\uD83D\uDC67\u200D(?:\uD83D[\uDC66\uDC67])|\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFF\u200D(?:\uD83E\uDD1D\u200D\uD83D\uDC68(?:\uD83C[\uDFFB-\uDFFE])|\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFE\u200D(?:\uD83E\uDD1D\u200D\uD83D\uDC68(?:\uD83C[\uDFFB-\uDFFD\uDFFF])|\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFD\u200D(?:\uD83E\uDD1D\u200D\uD83D\uDC68(?:\uD83C[\uDFFB\uDFFC\uDFFE\uDFFF])|\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFC\u200D(?:\uD83E\uDD1D\u200D\uD83D\uDC68(?:\uD83C[\uDFFB\uDFFD-\uDFFF])|\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|(?:\uD83C\uDFFF\u200D[\u2695\u2696\u2708]|\uD83C\uDFFE\u200D[\u2695\u2696\u2708]|\uD83C\uDFFD\u200D[\u2695\u2696\u2708]|\uD83C\uDFFC\u200D[\u2695\u2696\u2708]|\u200D[\u2695\u2696\u2708])\uFE0F|\u200D(?:(?:\uD83D[\uDC68\uDC69])\u200D(?:\uD83D[\uDC66\uDC67])|\uD83D[\uDC66\uDC67])|\uD83C\uDFFF|\uD83C\uDFFE|\uD83C\uDFFD|\uD83C\uDFFC)?|(?:\uD83D\uDC69(?:\uD83C\uDFFB\u200D\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D(?:\uD83D[\uDC68\uDC69])|\uD83D[\uDC68\uDC69])|(?:\uD83C[\uDFFC-\uDFFF])\u200D\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D(?:\uD83D[\uDC68\uDC69])|\uD83D[\uDC68\uDC69]))|\uD83E\uDDD1(?:\uD83C[\uDFFB-\uDFFF])\u200D\uD83E\uDD1D\u200D\uD83E\uDDD1)(?:\uD83C[\uDFFB-\uDFFF])|\uD83D\uDC69\u200D\uD83D\uDC69\u200D(?:\uD83D\uDC66\u200D\uD83D\uDC66|\uD83D\uDC67\u200D(?:\uD83D[\uDC66\uDC67]))|\uD83D\uDC69(?:\u200D(?:\u2764\uFE0F\u200D(?:\uD83D\uDC8B\u200D(?:\uD83D[\uDC68\uDC69])|\uD83D[\uDC68\uDC69])|\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFF\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFE\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFD\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFC\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFB\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD]))|\uD83E\uDDD1(?:\u200D(?:\uD83E\uDD1D\u200D\uD83E\uDDD1|\uD83C[\uDF3E\uDF73\uDF7C\uDF84\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFF\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF84\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFE\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF84\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFD\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF84\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFC\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF84\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD])|\uD83C\uDFFB\u200D(?:\uD83C[\uDF3E\uDF73\uDF7C\uDF84\uDF93\uDFA4\uDFA8\uDFEB\uDFED]|\uD83D[\uDCBB\uDCBC\uDD27\uDD2C\uDE80\uDE92]|\uD83E[\uDDAF-\uDDB3\uDDBC\uDDBD]))|\uD83D\uDC69\u200D\uD83D\uDC66\u200D\uD83D\uDC66|\uD83D\uDC69\u200D\uD83D\uDC69\u200D(?:\uD83D[\uDC66\uDC67])|\uD83D\uDC69\u200D\uD83D\uDC67\u200D(?:\uD83D[\uDC66\uDC67])|(?:\uD83D\uDC41\uFE0F\u200D\uD83D\uDDE8|\uD83E\uDDD1(?:\uD83C\uDFFF\u200D[\u2695\u2696\u2708]|\uD83C\uDFFE\u200D[\u2695\u2696\u2708]|\uD83C\uDFFD\u200D[\u2695\u2696\u2708]|\uD83C\uDFFC\u200D[\u2695\u2696\u2708]|\uD83C\uDFFB\u200D[\u2695\u2696\u2708]|\u200D[\u2695\u2696\u2708])|\uD83D\uDC69(?:\uD83C\uDFFF\u200D[\u2695\u2696\u2708]|\uD83C\uDFFE\u200D[\u2695\u2696\u2708]|\uD83C\uDFFD\u200D[\u2695\u2696\u2708]|\uD83C\uDFFC\u200D[\u2695\u2696\u2708]|\uD83C\uDFFB\u200D[\u2695\u2696\u2708]|\u200D[\u2695\u2696\u2708])|\uD83D\uDE36\u200D\uD83C\uDF2B|\uD83C\uDFF3\uFE0F\u200D\u26A7|\uD83D\uDC3B\u200D\u2744|(?:(?:\uD83C[\uDFC3\uDFC4\uDFCA]|\uD83D[\uDC6E\uDC70\uDC71\uDC73\uDC77\uDC81\uDC82\uDC86\uDC87\uDE45-\uDE47\uDE4B\uDE4D\uDE4E\uDEA3\uDEB4-\uDEB6]|\uD83E[\uDD26\uDD35\uDD37-\uDD39\uDD3D\uDD3E\uDDB8\uDDB9\uDDCD-\uDDCF\uDDD4\uDDD6-\uDDDD])(?:\uD83C[\uDFFB-\uDFFF])|\uD83D\uDC6F|\uD83E[\uDD3C\uDDDE\uDDDF])\u200D[\u2640\u2642]|(?:\u26F9|\uD83C[\uDFCB\uDFCC]|\uD83D\uDD75)(?:\uFE0F|\uD83C[\uDFFB-\uDFFF])\u200D[\u2640\u2642]|\uD83C\uDFF4\u200D\u2620|(?:\uD83C[\uDFC3\uDFC4\uDFCA]|\uD83D[\uDC6E\uDC70\uDC71\uDC73\uDC77\uDC81\uDC82\uDC86\uDC87\uDE45-\uDE47\uDE4B\uDE4D\uDE4E\uDEA3\uDEB4-\uDEB6]|\uD83E[\uDD26\uDD35\uDD37-\uDD39\uDD3D\uDD3E\uDDB8\uDDB9\uDDCD-\uDDCF\uDDD4\uDDD6-\uDDDD])\u200D[\u2640\u2642]|[\xA9\xAE\u203C\u2049\u2122\u2139\u2194-\u2199\u21A9\u21AA\u2328\u23CF\u23ED-\u23EF\u23F1\u23F2\u23F8-\u23FA\u24C2\u25AA\u25AB\u25B6\u25C0\u25FB\u25FC\u2600-\u2604\u260E\u2611\u2618\u2620\u2622\u2623\u2626\u262A\u262E\u262F\u2638-\u263A\u2640\u2642\u265F\u2660\u2663\u2665\u2666\u2668\u267B\u267E\u2692\u2694-\u2697\u2699\u269B\u269C\u26A0\u26A7\u26B0\u26B1\u26C8\u26CF\u26D1\u26D3\u26E9\u26F0\u26F1\u26F4\u26F7\u26F8\u2702\u2708\u2709\u270F\u2712\u2714\u2716\u271D\u2721\u2733\u2734\u2744\u2747\u2763\u27A1\u2934\u2935\u2B05-\u2B07\u3030\u303D\u3297\u3299]|\uD83C[\uDD70\uDD71\uDD7E\uDD7F\uDE02\uDE37\uDF21\uDF24-\uDF2C\uDF36\uDF7D\uDF96\uDF97\uDF99-\uDF9B\uDF9E\uDF9F\uDFCD\uDFCE\uDFD4-\uDFDF\uDFF5\uDFF7]|\uD83D[\uDC3F\uDCFD\uDD49\uDD4A\uDD6F\uDD70\uDD73\uDD76-\uDD79\uDD87\uDD8A-\uDD8D\uDDA5\uDDA8\uDDB1\uDDB2\uDDBC\uDDC2-\uDDC4\uDDD1-\uDDD3\uDDDC-\uDDDE\uDDE1\uDDE3\uDDE8\uDDEF\uDDF3\uDDFA\uDECB\uDECD-\uDECF\uDEE0-\uDEE5\uDEE9\uDEF0\uDEF3])\uFE0F|\uD83C\uDFF3\uFE0F\u200D\uD83C\uDF08|\uD83D\uDC69\u200D\uD83D\uDC67|\uD83D\uDC69\u200D\uD83D\uDC66|\uD83D\uDE35\u200D\uD83D\uDCAB|\uD83D\uDE2E\u200D\uD83D\uDCA8|\uD83D\uDC15\u200D\uD83E\uDDBA|\uD83E\uDDD1(?:\uD83C\uDFFF|\uD83C\uDFFE|\uD83C\uDFFD|\uD83C\uDFFC|\uD83C\uDFFB)?|\uD83D\uDC69(?:\uD83C\uDFFF|\uD83C\uDFFE|\uD83C\uDFFD|\uD83C\uDFFC|\uD83C\uDFFB)?|\uD83C\uDDFD\uD83C\uDDF0|\uD83C\uDDF6\uD83C\uDDE6|\uD83C\uDDF4\uD83C\uDDF2|\uD83D\uDC08\u200D\u2B1B|\u2764\uFE0F\u200D(?:\uD83D\uDD25|\uD83E\uDE79)|\uD83D\uDC41\uFE0F|\uD83C\uDFF3\uFE0F|\uD83C\uDDFF(?:\uD83C[\uDDE6\uDDF2\uDDFC])|\uD83C\uDDFE(?:\uD83C[\uDDEA\uDDF9])|\uD83C\uDDFC(?:\uD83C[\uDDEB\uDDF8])|\uD83C\uDDFB(?:\uD83C[\uDDE6\uDDE8\uDDEA\uDDEC\uDDEE\uDDF3\uDDFA])|\uD83C\uDDFA(?:\uD83C[\uDDE6\uDDEC\uDDF2\uDDF3\uDDF8\uDDFE\uDDFF])|\uD83C\uDDF9(?:\uD83C[\uDDE6\uDDE8\uDDE9\uDDEB-\uDDED\uDDEF-\uDDF4\uDDF7\uDDF9\uDDFB\uDDFC\uDDFF])|\uD83C\uDDF8(?:\uD83C[\uDDE6-\uDDEA\uDDEC-\uDDF4\uDDF7-\uDDF9\uDDFB\uDDFD-\uDDFF])|\uD83C\uDDF7(?:\uD83C[\uDDEA\uDDF4\uDDF8\uDDFA\uDDFC])|\uD83C\uDDF5(?:\uD83C[\uDDE6\uDDEA-\uDDED\uDDF0-\uDDF3\uDDF7-\uDDF9\uDDFC\uDDFE])|\uD83C\uDDF3(?:\uD83C[\uDDE6\uDDE8\uDDEA-\uDDEC\uDDEE\uDDF1\uDDF4\uDDF5\uDDF7\uDDFA\uDDFF])|\uD83C\uDDF2(?:\uD83C[\uDDE6\uDDE8-\uDDED\uDDF0-\uDDFF])|\uD83C\uDDF1(?:\uD83C[\uDDE6-\uDDE8\uDDEE\uDDF0\uDDF7-\uDDFB\uDDFE])|\uD83C\uDDF0(?:\uD83C[\uDDEA\uDDEC-\uDDEE\uDDF2\uDDF3\uDDF5\uDDF7\uDDFC\uDDFE\uDDFF])|\uD83C\uDDEF(?:\uD83C[\uDDEA\uDDF2\uDDF4\uDDF5])|\uD83C\uDDEE(?:\uD83C[\uDDE8-\uDDEA\uDDF1-\uDDF4\uDDF6-\uDDF9])|\uD83C\uDDED(?:\uD83C[\uDDF0\uDDF2\uDDF3\uDDF7\uDDF9\uDDFA])|\uD83C\uDDEC(?:\uD83C[\uDDE6\uDDE7\uDDE9-\uDDEE\uDDF1-\uDDF3\uDDF5-\uDDFA\uDDFC\uDDFE])|\uD83C\uDDEB(?:\uD83C[\uDDEE-\uDDF0\uDDF2\uDDF4\uDDF7])|\uD83C\uDDEA(?:\uD83C[\uDDE6\uDDE8\uDDEA\uDDEC\uDDED\uDDF7-\uDDFA])|\uD83C\uDDE9(?:\uD83C[\uDDEA\uDDEC\uDDEF\uDDF0\uDDF2\uDDF4\uDDFF])|\uD83C\uDDE8(?:\uD83C[\uDDE6\uDDE8\uDDE9\uDDEB-\uDDEE\uDDF0-\uDDF5\uDDF7\uDDFA-\uDDFF])|\uD83C\uDDE7(?:\uD83C[\uDDE6\uDDE7\uDDE9-\uDDEF\uDDF1-\uDDF4\uDDF6-\uDDF9\uDDFB\uDDFC\uDDFE\uDDFF])|\uD83C\uDDE6(?:\uD83C[\uDDE8-\uDDEC\uDDEE\uDDF1\uDDF2\uDDF4\uDDF6-\uDDFA\uDDFC\uDDFD\uDDFF])|[#*0-9]\uFE0F\u20E3|\u2764\uFE0F|(?:\uD83C[\uDFC3\uDFC4\uDFCA]|\uD83D[\uDC6E\uDC70\uDC71\uDC73\uDC77\uDC81\uDC82\uDC86\uDC87\uDE45-\uDE47\uDE4B\uDE4D\uDE4E\uDEA3\uDEB4-\uDEB6]|\uD83E[\uDD26\uDD35\uDD37-\uDD39\uDD3D\uDD3E\uDDB8\uDDB9\uDDCD-\uDDCF\uDDD4\uDDD6-\uDDDD])(?:\uD83C[\uDFFB-\uDFFF])|(?:\u26F9|\uD83C[\uDFCB\uDFCC]|\uD83D\uDD75)(?:\uFE0F|\uD83C[\uDFFB-\uDFFF])|\uD83C\uDFF4|(?:[\u270A\u270B]|\uD83C[\uDF85\uDFC2\uDFC7]|\uD83D[\uDC42\uDC43\uDC46-\uDC50\uDC66\uDC67\uDC6B-\uDC6D\uDC72\uDC74-\uDC76\uDC78\uDC7C\uDC83\uDC85\uDC8F\uDC91\uDCAA\uDD7A\uDD95\uDD96\uDE4C\uDE4F\uDEC0\uDECC]|\uD83E[\uDD0C\uDD0F\uDD18-\uDD1C\uDD1E\uDD1F\uDD30-\uDD34\uDD36\uDD77\uDDB5\uDDB6\uDDBB\uDDD2\uDDD3\uDDD5])(?:\uD83C[\uDFFB-\uDFFF])|(?:[\u261D\u270C\u270D]|\uD83D[\uDD74\uDD90])(?:\uFE0F|\uD83C[\uDFFB-\uDFFF])|[\u270A\u270B]|\uD83C[\uDF85\uDFC2\uDFC7]|\uD83D[\uDC08\uDC15\uDC3B\uDC42\uDC43\uDC46-\uDC50\uDC66\uDC67\uDC6B-\uDC6D\uDC72\uDC74-\uDC76\uDC78\uDC7C\uDC83\uDC85\uDC8F\uDC91\uDCAA\uDD7A\uDD95\uDD96\uDE2E\uDE35\uDE36\uDE4C\uDE4F\uDEC0\uDECC]|\uD83E[\uDD0C\uDD0F\uDD18-\uDD1C\uDD1E\uDD1F\uDD30-\uDD34\uDD36\uDD77\uDDB5\uDDB6\uDDBB\uDDD2\uDDD3\uDDD5]|\uD83C[\uDFC3\uDFC4\uDFCA]|\uD83D[\uDC6E\uDC70\uDC71\uDC73\uDC77\uDC81\uDC82\uDC86\uDC87\uDE45-\uDE47\uDE4B\uDE4D\uDE4E\uDEA3\uDEB4-\uDEB6]|\uD83E[\uDD26\uDD35\uDD37-\uDD39\uDD3D\uDD3E\uDDB8\uDDB9\uDDCD-\uDDCF\uDDD4\uDDD6-\uDDDD]|\uD83D\uDC6F|\uD83E[\uDD3C\uDDDE\uDDDF]|[\u231A\u231B\u23E9-\u23EC\u23F0\u23F3\u25FD\u25FE\u2614\u2615\u2648-\u2653\u267F\u2693\u26A1\u26AA\u26AB\u26BD\u26BE\u26C4\u26C5\u26CE\u26D4\u26EA\u26F2\u26F3\u26F5\u26FA\u26FD\u2705\u2728\u274C\u274E\u2753-\u2755\u2757\u2795-\u2797\u27B0\u27BF\u2B1B\u2B1C\u2B50\u2B55]|\uD83C[\uDC04\uDCCF\uDD8E\uDD91-\uDD9A\uDE01\uDE1A\uDE2F\uDE32-\uDE36\uDE38-\uDE3A\uDE50\uDE51\uDF00-\uDF20\uDF2D-\uDF35\uDF37-\uDF7C\uDF7E-\uDF84\uDF86-\uDF93\uDFA0-\uDFC1\uDFC5\uDFC6\uDFC8\uDFC9\uDFCF-\uDFD3\uDFE0-\uDFF0\uDFF8-\uDFFF]|\uD83D[\uDC00-\uDC07\uDC09-\uDC14\uDC16-\uDC3A\uDC3C-\uDC3E\uDC40\uDC44\uDC45\uDC51-\uDC65\uDC6A\uDC79-\uDC7B\uDC7D-\uDC80\uDC84\uDC88-\uDC8E\uDC90\uDC92-\uDCA9\uDCAB-\uDCFC\uDCFF-\uDD3D\uDD4B-\uDD4E\uDD50-\uDD67\uDDA4\uDDFB-\uDE2D\uDE2F-\uDE34\uDE37-\uDE44\uDE48-\uDE4A\uDE80-\uDEA2\uDEA4-\uDEB3\uDEB7-\uDEBF\uDEC1-\uDEC5\uDED0-\uDED2\uDED5-\uDED7\uDEEB\uDEEC\uDEF4-\uDEFC\uDFE0-\uDFEB]|\uD83E[\uDD0D\uDD0E\uDD10-\uDD17\uDD1D\uDD20-\uDD25\uDD27-\uDD2F\uDD3A\uDD3F-\uDD45\uDD47-\uDD76\uDD78\uDD7A-\uDDB4\uDDB7\uDDBA\uDDBC-\uDDCB\uDDD0\uDDE0-\uDDFF\uDE70-\uDE74\uDE78-\uDE7A\uDE80-\uDE86\uDE90-\uDEA8\uDEB0-\uDEB6\uDEC0-\uDEC2\uDED0-\uDED6]|(?:[#*0-9\xA9\xAE\u203C\u2049\u2122\u2139\u2194-\u2199\u21A9\u21AA\u231A\u231B\u2328\u23CF\u23E9-\u23F3\u23F8-\u23FA\u24C2\u25AA\u25AB\u25B6\u25C0\u25FB-\u25FE\u2600-\u2604\u260E\u2611\u2614\u2615\u2618\u261D\u2620\u2622\u2623\u2626\u262A\u262E\u262F\u2638-\u263A\u2640\u2642\u2648-\u2653\u265F\u2660\u2663\u2665\u2666\u2668\u267B\u267E\u267F\u2692-\u2697\u2699\u269B\u269C\u26A0\u26A1\u26A7\u26AA\u26AB\u26B0\u26B1\u26BD\u26BE\u26C4\u26C5\u26C8\u26CE\u26CF\u26D1\u26D3\u26D4\u26E9\u26EA\u26F0-\u26F5\u26F7-\u26FA\u26FD\u2702\u2705\u2708-\u270D\u270F\u2712\u2714\u2716\u271D\u2721\u2728\u2733\u2734\u2744\u2747\u274C\u274E\u2753-\u2755\u2757\u2763\u2764\u2795-\u2797\u27A1\u27B0\u27BF\u2934\u2935\u2B05-\u2B07\u2B1B\u2B1C\u2B50\u2B55\u3030\u303D\u3297\u3299]|\uD83C[\uDC04\uDCCF\uDD70\uDD71\uDD7E\uDD7F\uDD8E\uDD91-\uDD9A\uDDE6-\uDDFF\uDE01\uDE02\uDE1A\uDE2F\uDE32-\uDE3A\uDE50\uDE51\uDF00-\uDF21\uDF24-\uDF93\uDF96\uDF97\uDF99-\uDF9B\uDF9E-\uDFF0\uDFF3-\uDFF5\uDFF7-\uDFFF]|\uD83D[\uDC00-\uDCFD\uDCFF-\uDD3D\uDD49-\uDD4E\uDD50-\uDD67\uDD6F\uDD70\uDD73-\uDD7A\uDD87\uDD8A-\uDD8D\uDD90\uDD95\uDD96\uDDA4\uDDA5\uDDA8\uDDB1\uDDB2\uDDBC\uDDC2-\uDDC4\uDDD1-\uDDD3\uDDDC-\uDDDE\uDDE1\uDDE3\uDDE8\uDDEF\uDDF3\uDDFA-\uDE4F\uDE80-\uDEC5\uDECB-\uDED2\uDED5-\uDED7\uDEE0-\uDEE5\uDEE9\uDEEB\uDEEC\uDEF0\uDEF3-\uDEFC\uDFE0-\uDFEB]|\uD83E[\uDD0C-\uDD3A\uDD3C-\uDD45\uDD47-\uDD78\uDD7A-\uDDCB\uDDCD-\uDDFF\uDE70-\uDE74\uDE78-\uDE7A\uDE80-\uDE86\uDE90-\uDEA8\uDEB0-\uDEB6\uDEC0-\uDEC2\uDED0-\uDED6]|☻|♡)\uFE0F?";
 
-let replacementListCache;
-const unicodeRegexpCache = {};
-
-function replacementList() {
-  if (replacementListCache === undefined) {
-    replacementListCache = buildReplacementsList(replacements);
-  }
-
-  return replacementListCache;
-}
-
-function unicodeRegexp(inlineEmoji) {
-  if (unicodeRegexpCache[inlineEmoji] === undefined) {
-    const emojiExpression = inlineEmoji
-      ? "|:[^\\s:]+(?::t\\d)?:?"
-      : "|\\B:[^\\s:]+(?::t\\d)?:?\\B";
-
-    unicodeRegexpCache[inlineEmoji] = new RegExp(
-      replacementList() + emojiExpression,
-      "g"
-    );
-  }
-
-  return unicodeRegexpCache[inlineEmoji];
+function textEmojiRegex(inlineEmoji) {
+  return inlineEmoji ? /:[^\s:]+(?::t\d)?:?/g : /\B:[^\s:]+(?::t\d)?:?\B/g;
 }
 
 // add all default emojis
@@ -83,7 +50,7 @@ function isReplacableInlineEmoji(string, index, inlineEmoji) {
   return (
     beforeEmoji.length === 0 ||
     /(?:\s|[>.,\/#!$%^&*;:{}=\-_`~()])$/.test(beforeEmoji) ||
-    new RegExp(`(?:${replacementList()})$`).test(beforeEmoji)
+    new RegExp(`(?:${emojiReplacementRegex})$`, "g").test(beforeEmoji)
   );
 }
 
@@ -92,18 +59,17 @@ export function performEmojiUnescape(string, opts) {
     return;
   }
 
-  const inlineEmoji = opts.inlineEmoji;
-  const regexp = unicodeRegexp(inlineEmoji);
   const allTranslations = Object.assign(
     {},
     translations,
     opts.customEmojiTranslation || {}
   );
 
-  return string.replace(regexp, (m, index) => {
+  const replacementFunction = (m, index) => {
     const isEmoticon = opts.enableEmojiShortcuts && !!allTranslations[m];
     const isUnicodeEmoticon = !!replacements[m];
     let emojiVal;
+
     if (isEmoticon) {
       emojiVal = allTranslations[m];
     } else if (isUnicodeEmoticon) {
@@ -123,7 +89,7 @@ export function performEmojiUnescape(string, opts) {
 
     const isReplacable =
       (isEmoticon || hasEndingColon || isUnicodeEmoticon) &&
-      isReplacableInlineEmoji(string, index, inlineEmoji);
+      isReplacableInlineEmoji(string, index, opts.inlineEmoji);
 
     return url && isReplacable
       ? `<img width="20" height="20" src='${url}' ${
@@ -132,20 +98,22 @@ export function performEmojiUnescape(string, opts) {
           opts.lazy ? "loading='lazy' " : ""
         }alt='${emojiVal}' class='${classes}'>`
       : m;
-  });
+  };
+
+  return string
+    .replace(new RegExp(emojiReplacementRegex, "g"), replacementFunction)
+    .replace(textEmojiRegex(opts.inlineEmoji), replacementFunction);
 }
 
 export function performEmojiEscape(string, opts) {
-  const inlineEmoji = opts.inlineEmoji;
-  const regexp = unicodeRegexp(inlineEmoji);
   const allTranslations = Object.assign(
     {},
     translations,
     opts.customEmojiTranslation || {}
   );
 
-  return string.replace(regexp, (m, index) => {
-    if (isReplacableInlineEmoji(string, index, inlineEmoji)) {
+  const replacementFunction = (m, index) => {
+    if (isReplacableInlineEmoji(string, index, opts.inlineEmoji)) {
       if (!!allTranslations[m]) {
         return opts.emojiShortcuts ? `:${allTranslations[m]}:` : m;
       } else if (!!replacements[m]) {
@@ -154,7 +122,11 @@ export function performEmojiEscape(string, opts) {
     }
 
     return m;
-  });
+  };
+
+  return string
+    .replace(new RegExp(emojiReplacementRegex, "g"), replacementFunction)
+    .replace(textEmojiRegex(opts.inlineEmoji), replacementFunction);
 }
 
 export function isCustomEmoji(code, opts) {
diff --git a/app/assets/javascripts/pretty-text/addon/emoji/data.js b/app/assets/javascripts/pretty-text/addon/emoji/data.js
index f23158ec22..aaf4f4da14 100644
--- a/app/assets/javascripts/pretty-text/addon/emoji/data.js
+++ b/app/assets/javascripts/pretty-text/addon/emoji/data.js
@@ -48,8 +48,7 @@ export const emojis = [
   "rage",
   "pensive",
   "confused",
-  "slightly_frowning_face",
-  "frowning_face",
+  "frowning",
   "persevere",
   "confounded",
   "tired_face",
@@ -60,7 +59,7 @@ export const emojis = [
   "fearful",
   "cold_sweat",
   "hushed",
-  "frowning",
+  "slightly_frowning_face",
   "frowning_face_with_open_mouth",
   "anguished",
   "cry",
@@ -1829,6 +1828,7 @@ export const tonableEmojis = [
   "palms_up_together",
 ];
 export const aliases = {
+  grinning_face_with_smiling_eyes: ["smile"],
   right_anger_bubble: ["anger_right"],
   ballot_box: ["ballot_box_with_ballot"],
   basketball_man: ["basketball_player", "person_with_ball"],
@@ -1920,7 +1920,6 @@ export const aliases = {
     "white_sun_rain_cloud",
     "white_sun_behind_cloud_with_rain",
   ],
-  grinning_face_with_smiling_eyes: ["smile"],
   partly_sunny: ["white_sun_small_cloud", "white_sun_with_small_cloud"],
   open_umbrella: ["umbrella2"],
   hammer_and_wrench: ["tools"],
@@ -1936,8 +1935,8 @@ export const aliases = {
   nerd_face: ["nerd"],
   hugs: ["hugging", "hugging_face"],
   roll_eyes: ["rolling_eyes", "face_with_rolling_eyes"],
-  slightly_frowning_face: ["slight_frown"],
-  frowning_face: ["frowning2", "white_frowning_face"],
+  slightly_frowning_face: ["slight_frown", "slightly_frowning"],
+  frowning: ["frowning2", "white_frowning_face", "frowning_face"],
   zipper_mouth_face: ["zipper_mouth"],
   face_with_head_bandage: ["head_bandage"],
   raised_hand_with_fingers_splayed: ["hand_splayed"],
@@ -2083,7 +2082,7 @@ export const replacements = {
   "😊": "blush",
   "🙂": "slightly_smiling_face",
   "🙃": "upside_down_face",
-  "☺": "slight_smile",
+  "☺": "relaxed",
   "😋": "yum",
   "😌": "relieved",
   "😍": "heart_eyes",
@@ -2115,8 +2114,7 @@ export const replacements = {
   "😡": "rage",
   "😔": "pensive",
   "😕": "confused",
-  "☹️": "slightly_frowning_face",
-  "🙁": "frowning",
+  "🙁": "slightly_frowning_face",
   "😣": "persevere",
   "😖": "confounded",
   "😫": "tired_face",
@@ -3708,7 +3706,7 @@ export const replacements = {
   "🖌": "paintbrush",
   "🔍": "mag",
   "🔎": "mag_right",
-  "❤": "heart",
+  "❤️": "heart",
   "💛": "yellow_heart",
   "💚": "green_heart",
   "💙": "blue_heart",
@@ -3944,7 +3942,6 @@ export const replacements = {
   "🀄": "mahjong",
   "♠": "spades",
   "♣": "clubs",
-  "♥": "heart",
   "♦": "diamonds",
   "🎴": "flower_playing_cards",
   "💭": "thought_balloon",
@@ -4539,19 +4536,18 @@ export const replacements = {
   "👨‍🦼": "man_in_motorized_wheelchair",
   "👩‍🦯": "woman_with_probing_cane",
   "👨‍🦯": "man_with_probing_cane",
-  "🧎‍♀": "woman_kneeling",
-  "🧎‍♂": "man_kneeling",
-  "🧍‍♂": "man_standing",
-  "🧍‍♀": "woman_standing",
-  "🧏‍♀": "deaf_woman",
-  "🧏‍♂": "deaf_man",
+  "🧎‍♀️": "woman_kneeling",
+  "🧎‍♂️": "man_kneeling",
+  "🧍‍♂️": "man_standing",
+  "🧍‍♀️": "woman_standing",
+  "🧏‍♀️": "deaf_woman",
+  "🧏‍♂️": "deaf_man",
   "🦻": "hear_with_hearing_aid",
   "🦿": "mechanical_leg",
   "🦾": "mechanical_arm",
   "🤍": "white_heart",
   "🤎": "brown_heart",
-  "🏳️‍⚧": "transgender_flag",
-  "☹": "frowning",
+  "🏳️‍⚧️": "transgender_flag",
+  "☹️": "frowning",
   "☻": "slight_smile",
-  "♡": "heart",
 };
diff --git a/lib/emoji/db.json b/lib/emoji/db.json
index 5f7c778fd2..3e3ee9235d 100644
--- a/lib/emoji/db.json
+++ b/lib/emoji/db.json
@@ -60,6 +60,10 @@
       "code": "263a",
       "name": "relaxed"
     },
+    {
+      "code": "263b",
+      "name": "slight_smile"
+    },
     {
       "code": "1f60b",
       "name": "yum"
@@ -185,12 +189,12 @@
       "name": "confused"
     },
     {
-      "code": "2639-fe0f",
-      "name": "slightly_frowning_face"
+      "code": "2639",
+      "name": "frowning"
     },
     {
       "code": "1f641",
-      "name": "frowning_face"
+      "name": "slightly_frowning_face"
     },
     {
       "code": "1f623",
@@ -232,10 +236,6 @@
       "code": "1f62f",
       "name": "hushed"
     },
-    {
-      "code": "1f641",
-      "name": "frowning"
-    },
     {
       "code": "1f626",
       "name": "frowning_face_with_open_mouth"
@@ -3664,6 +3664,10 @@
       "code": "2764",
       "name": "heart"
     },
+    {
+      "code": "2661",
+      "name": "white_heart_suit"
+    },
     {
       "code": "1f49b",
       "name": "yellow_heart"
diff --git a/lib/emoji/groups.json b/lib/emoji/groups.json
index 0c18098dda..c8604627f4 100644
--- a/lib/emoji/groups.json
+++ b/lib/emoji/groups.json
@@ -263,10 +263,6 @@
         "name": "slightly_frowning_face",
         "diversity": false
       },
-      {
-        "name": "frowning_face",
-        "diversity": false
-      },
       {
         "name": "open_mouth",
         "diversity": false
diff --git a/lib/pretty_text/shims.js b/lib/pretty_text/shims.js
index 4c9de85dfc..bc281c23bc 100644
--- a/lib/pretty_text/shims.js
+++ b/lib/pretty_text/shims.js
@@ -1,7 +1,7 @@
 __PrettyText = require("pretty-text/pretty-text").default;
 __buildOptions = require("pretty-text/pretty-text").buildOptions;
 __performEmojiUnescape = require("pretty-text/emoji").performEmojiUnescape;
-__buildReplacementsList = require("pretty-text/emoji").buildReplacementsList;
+__emojiReplacementRegex = require("pretty-text/emoji").emojiReplacementRegex;
 __performEmojiEscape = require("pretty-text/emoji").performEmojiEscape;
 __resetTranslationTree = require("pretty-text/engines/discourse-markdown/emoji")
   .resetTranslationTree;
@@ -28,18 +28,34 @@ __utils = require("discourse/lib/utilities");
 __emojiUnicodeReplacer = null;
 
 __setUnicode = function (replacements) {
-  let unicodeRegexp = new RegExp(__buildReplacementsList(replacements), "g");
+  const regexp = new RegExp(__emojiReplacementRegex, "g");
 
   __emojiUnicodeReplacer = function (text) {
-    unicodeRegexp.lastIndex = 0;
+    regexp.lastIndex = 0;
+
     let m;
-    while ((m = unicodeRegexp.exec(text)) !== null) {
-      let replacement = ":" + replacements[m[0]] + ":";
+    while ((m = regexp.exec(text)) !== null) {
+      let match = m[0];
+
+      let replacement = replacements[match];
+
+      if (!replacement) {
+        // if we can't find replacement for an emoji match
+        // attempts to look for the same without trailing variation selector
+        match = match.replace(/\ufe0f$/g, "");
+        replacement = replacements[match];
+      }
+
+      if (!replacement) {
+        continue;
+      }
+
+      replacement = ":" + replacement + ":";
       const before = text.charAt(m.index - 1);
       if (!/\B/.test(before)) {
         replacement = "\u200b" + replacement;
       }
-      text = text.replace(m[0], replacement);
+      text = text.replace(match, replacement);
     }
 
     // fixes Safari VARIATION SELECTOR-16 issue with some emojis
@@ -53,7 +69,9 @@ __setUnicode = function (replacements) {
 __paths = {};
 
 function __getURLNoCDN(url) {
-  if (!url) return url;
+  if (!url) {
+    return url;
+  }
 
   // if it's a non relative URL, return it.
   if (url !== "/" && !/^\/[^\/]/.test(url)) {
@@ -63,7 +81,9 @@ function __getURLNoCDN(url) {
   if (url.indexOf(__paths.baseUri) !== -1) {
     return url;
   }
-  if (url[0] !== "/") url = "/" + url;
+  if (url[0] !== "/") {
+    url = "/" + url;
+  }
 
   return __paths.baseUri + url;
 }
diff --git a/spec/components/pretty_text_spec.rb b/spec/components/pretty_text_spec.rb
index 3baaa24ba7..93441ba4dd 100644
--- a/spec/components/pretty_text_spec.rb
+++ b/spec/components/pretty_text_spec.rb
@@ -112,6 +112,7 @@ describe PrettyText do
 
         it "adds an only-emoji class when a line has only one emoji" do
           md = <<~MD
+            ☹️
             foo 😀
             foo 😀 bar
             :smile_cat:
@@ -131,7 +132,8 @@ describe PrettyText do
           MD
 
           html = <<~HTML
-            <p>foo <img src="/images/emoji/twitter/grinning.png?v=#{Emoji::EMOJI_VERSION}" title=":grinning:" class="emoji" alt=":grinning:"><br>
+            <p><img src="/images/emoji/twitter/frowning.png?v=#{Emoji::EMOJI_VERSION}" title=":frowning:" class="emoji only-emoji" alt=":frowning:"><br>
+            foo <img src="/images/emoji/twitter/grinning.png?v=#{Emoji::EMOJI_VERSION}" title=":grinning:" class="emoji" alt=":grinning:"><br>
             foo <img src="/images/emoji/twitter/grinning.png?v=#{Emoji::EMOJI_VERSION}" title=":grinning:" class="emoji" alt=":grinning:"> bar<br>
             <img src="/images/emoji/twitter/smile_cat.png?v=#{Emoji::EMOJI_VERSION}" title=":smile_cat:" class="emoji only-emoji" alt=":smile_cat:"><br>
             <img src="/images/emoji/twitter/smile_cat.png?v=#{Emoji::EMOJI_VERSION}" title=":smile_cat:" class="emoji only-emoji" alt=":smile_cat:"> <img src="/images/emoji/twitter/smile_cat.png?v=#{Emoji::EMOJI_VERSION}" title=":smile_cat:" class="emoji only-emoji" alt=":smile_cat:"><br>
@@ -1109,7 +1111,12 @@ describe PrettyText do
     end
 
     it "replaces some glyphs that are not in the emoji range" do
+      expect(PrettyText.cook("☹")).to match(/\:frowning\:/)
       expect(PrettyText.cook("☺")).to match(/\:relaxed\:/)
+      expect(PrettyText.cook("☻")).to match(/\:slight_smile\:/)
+      expect(PrettyText.cook("♡")).to match(/\:heart\:/)
+      expect(PrettyText.cook("❤")).to match(/\:heart\:/)
+      expect(PrettyText.cook("❤️")).to match(/\:heart\:/) # in emoji range but ensure it works along others
     end
 
     it "replaces digits" do