diff --git a/packages/message-parser/src/grammar.pegjs b/packages/message-parser/src/grammar.pegjs
index a6cae97facbf..2d007e957d6a 100644
--- a/packages/message-parser/src/grammar.pegjs
+++ b/packages/message-parser/src/grammar.pegjs
@@ -342,9 +342,15 @@ AutolinkedEmail = e:Email { return autoEmail(e); }
  * with customDomains options as intranet: protocol://internaltool.intranet
  *
  */
-AutolinkedURL = u:AutoLinkURL { return autoLink(u, options.customDomains); }
+AutolinkedURL
+  = s:openPunctuation u:AutolinkedURL_urlDelimitedByPunctuation e:closePunctuation { return [plain(s), autoLink(u, options.customDomains), plain(e)]; }
+  / u:AutolinkedURL_url { return autoLink(u, options.customDomains); }
 
-AutoLinkURL
+AutolinkedURL_urlDelimitedByPunctuation
+  = $(URLScheme URLAuthority (!closePunctuation .)*)
+  / $(URLAuthorityHost (!closePunctuation .)*)
+
+AutolinkedURL_url
   = $(URLScheme URLAuthority AutoLinkURLBody*)
   / $(URLAuthorityHost AutoLinkURLBody*)
 
@@ -729,3 +735,7 @@ DecimalNumberChar = [0-9\u0660-\u0669\u06F0-\u06F9\u07C0-\u07C9\u0966-\u096F\u09
 EmojiChar = [\u2700-\u27bf\udde6-\uddff\ud800-\udbff\udc00-\udfff\ufe0e\ufe0f\u0300-\u036f\ufe20-\ufe23\u20d0-\u20f0\ud83c\udffb-\udfff\u200d\u3299\u3297\u303d\u3030\u24c2\ud83c\udd70-\udd71\udd7e-\udd7f\udd8e\udd91-\udd9a\udde6-\uddff\ude01-\ude02\ude1a\ude2f\ude32-\ude3a\ude50-\ude51\u203c\u2049\u25aa-\u25ab\u25b6\u25c0\u25fb-\u25fe\u00a9\u00ae\u2122\u2139\udc04\u2600-\u26FF\u2b05\u2b06\u2b07\u2b1b\u2b1c\u2b50\u2b55\u231a\u231b\u2328\u23cf\u23e9-\u23f3\u23f8-\u23fa\udccf\u2935\u2934\u2190-\u21ff]
 
 MarkChar = [\u0300-\u036F\u0483-\u0489\u0591-\u05BD\u05BF\u05C1\u05C2\u05C4\u05C5\u05C7\u0610-\u061A\u064B-\u065F\u0670\u06D6-\u06DC\u06DF-\u06E4\u06E7\u06E8\u06EA-\u06ED\u0711\u0730-\u074A\u07A6-\u07B0\u07EB-\u07F3\u0816-\u0819\u081B-\u0823\u0825-\u0827\u0829-\u082D\u0859-\u085B\u08D4-\u08E1\u08E3-\u0903\u093A-\u093C\u093E-\u094F\u0951-\u0957\u0962\u0963\u0981-\u0983\u09BC\u09BE-\u09C4\u09C7\u09C8\u09CB-\u09CD\u09D7\u09E2\u09E3\u0A01-\u0A03\u0A3C\u0A3E-\u0A42\u0A47\u0A48\u0A4B-\u0A4D\u0A51\u0A70\u0A71\u0A75\u0A81-\u0A83\u0ABC\u0ABE-\u0AC5\u0AC7-\u0AC9\u0ACB-\u0ACD\u0AE2\u0AE3\u0B01-\u0B03\u0B3C\u0B3E-\u0B44\u0B47\u0B48\u0B4B-\u0B4D\u0B56\u0B57\u0B62\u0B63\u0B82\u0BBE-\u0BC2\u0BC6-\u0BC8\u0BCA-\u0BCD\u0BD7\u0C00-\u0C03\u0C3E-\u0C44\u0C46-\u0C48\u0C4A-\u0C4D\u0C55\u0C56\u0C62\u0C63\u0C81-\u0C83\u0CBC\u0CBE-\u0CC4\u0CC6-\u0CC8\u0CCA-\u0CCD\u0CD5\u0CD6\u0CE2\u0CE3\u0D01-\u0D03\u0D3E-\u0D44\u0D46-\u0D48\u0D4A-\u0D4D\u0D57\u0D62\u0D63\u0D82\u0D83\u0DCA\u0DCF-\u0DD4\u0DD6\u0DD8-\u0DDF\u0DF2\u0DF3\u0E31\u0E34-\u0E3A\u0E47-\u0E4E\u0EB1\u0EB4-\u0EB9\u0EBB\u0EBC\u0EC8-\u0ECD\u0F18\u0F19\u0F35\u0F37\u0F39\u0F3E\u0F3F\u0F71-\u0F84\u0F86\u0F87\u0F8D-\u0F97\u0F99-\u0FBC\u0FC6\u102B-\u103E\u1056-\u1059\u105E-\u1060\u1062-\u1064\u1067-\u106D\u1071-\u1074\u1082-\u108D\u108F\u109A-\u109D\u135D-\u135F\u1712-\u1714\u1732-\u1734\u1752\u1753\u1772\u1773\u17B4-\u17D3\u17DD\u180B-\u180D\u1885\u1886\u18A9\u1920-\u192B\u1930-\u193B\u1A17-\u1A1B\u1A55-\u1A5E\u1A60-\u1A7C\u1A7F\u1AB0-\u1ABE\u1B00-\u1B04\u1B34-\u1B44\u1B6B-\u1B73\u1B80-\u1B82\u1BA1-\u1BAD\u1BE6-\u1BF3\u1C24-\u1C37\u1CD0-\u1CD2\u1CD4-\u1CE8\u1CED\u1CF2-\u1CF4\u1CF8\u1CF9\u1DC0-\u1DF5\u1DFB-\u1DFF\u20D0-\u20F0\u2CEF-\u2CF1\u2D7F\u2DE0-\u2DFF\u302A-\u302F\u3099\u309A\uA66F-\uA672\uA674-\uA67D\uA69E\uA69F\uA6F0\uA6F1\uA802\uA806\uA80B\uA823-\uA827\uA880\uA881\uA8B4-\uA8C5\uA8E0-\uA8F1\uA926-\uA92D\uA947-\uA953\uA980-\uA983\uA9B3-\uA9C0\uA9E5\uAA29-\uAA36\uAA43\uAA4C\uAA4D\uAA7B-\uAA7D\uAAB0\uAAB2-\uAAB4\uAAB7\uAAB8\uAABE\uAABF\uAAC1\uAAEB-\uAAEF\uAAF5\uAAF6\uABE3-\uABEA\uABEC\uABED\uFB1E\uFE00-\uFE0F\uFE20-\uFE2F]
+
+openPunctuation = [\u0028\u005B\u007B\u0F3A\u0F3C\u169B\u201A\u201E\u2045\u207D\u208D\u2308\u230A\u2329\u2768\u276A\u276C\u276E\u2770\u2772\u2774\u27C5\u27E6\u27E8\u27EA\u27EC\u27EE\u2983\u2985\u2987\u2989\u298B\u298D\u298F\u2991\u2993\u2995\u2997\u29D8\u29DA\u29FC\u2E22\u2E24\u2E26\u2E28\u2E42\u3008\u300A\u300C\u300E\u3010\u3014\u3016\u3018\u301A\u301D\uFD3F\uFE17\uFE35\uFE37\uFE39\uFE3B\uFE3D\uFE3F\uFE41\uFE43\uFE47\uFE59\uFE5B\uFE5D\uFF08\uFF3B\uFF5B\uFF5F\uFF62]
+
+closePunctuation = [\u0029\u005D\u007D\u0F3B\u0F3D\u169C\u2046\u207E\u208E\u2309\u230B\u232A\u2769\u276B\u276D\u276F\u2771\u2773\u2775\u27C6\u27E7\u27E9\u27EB\u27ED\u27EF\u2984\u2986\u2988\u298A\u298C\u298E\u2990\u2992\u2994\u2996\u2998\u29D9\u29DB\u29FD\u2E23\u2E25\u2E27\u2E29\u3009\u300B\u300D\u300F\u3011\u3015\u3017\u3019\u301B\u301E\u301F\uFD3E\uFE18\uFE36\uFE38\uFE3A\uFE3C\uFE3E\uFE40\uFE42\uFE44\uFE48\uFE5A\uFE5C\uFE5E\uFF09\uFF3D\uFF5D\uFF60\uFF63]