diff --git a/packages/rocketchat-markdown/lib/parser/original/markdown.js b/packages/rocketchat-markdown/lib/parser/original/markdown.js
index db7105eb6183..0b7143d33e39 100644
--- a/packages/rocketchat-markdown/lib/parser/original/markdown.js
+++ b/packages/rocketchat-markdown/lib/parser/original/markdown.js
@@ -39,7 +39,7 @@ const parseNotEscaped = function(msg, message) {
 	}
 
 	// Support *text* to make bold
-	msg = msg.replace(/(^|&gt;|[ >_~`])\*{1,2}([^\*\r\n]+)\*{1,2}([<_~`]|\B|\b|$)/gm, '$1<span class="copyonly">*</span><strong>$2</strong><span class="copyonly">*</span>$3');
+	msg = msg.replace(/(|&gt;|[ >_~`])\*{1,2}([^\*\r\n]+)\*{1,2}([<_~`]|\B|\b|$)/gm, '$1<span class="copyonly">*</span><strong>$2</strong><span class="copyonly">*</span>$3');
 
 	// Support _text_ to make italics
 	msg = msg.replace(/(^|&gt;|[ >*~`])\_{1,2}([^\_\r\n]+)\_{1,2}([<*~`]|\B|\b|$)/gm, '$1<span class="copyonly">_</span><em>$2</em><span class="copyonly">_</span>$3');
diff --git a/packages/rocketchat-markdown/tests/client.tests.js b/packages/rocketchat-markdown/tests/client.tests.js
index c9867c271de6..54228ca9ef4c 100644
--- a/packages/rocketchat-markdown/tests/client.tests.js
+++ b/packages/rocketchat-markdown/tests/client.tests.js
@@ -26,14 +26,16 @@ const bold = {
 	'*Hello': '*Hello',
 	'Hello*': 'Hello*',
 	'He*llo': 'He*llo',
-	'***Hello***': '***Hello***',
-	'***Hello**': '***Hello**',
+	'***Hello***': `*${ boldWrapper('Hello') }*`,
+	'***Hello**': `*${ boldWrapper('Hello') }`,
 	'*Hello* this is dog': `${ boldWrapper('Hello') } this is dog`,
 	'Rocket cat says *Hello*': `Rocket cat says ${ boldWrapper('Hello') }`,
 	'He said *Hello* to her': `He said ${ boldWrapper('Hello') } to her`,
 	'**Hello** this is dog': `${ boldWrapper('Hello') } this is dog`,
 	'Rocket cat says **Hello**': `Rocket cat says ${ boldWrapper('Hello') }`,
 	'He said **Hello** to her': `He said ${ boldWrapper('Hello') } to her`,
+	'He was a**nn**oyed': `He was a${ boldWrapper('nn') }oyed`,
+	'There are two o in f*oo*tball': `There are two o in f${ boldWrapper('oo') }tball`,
 };
 
 const italic = {