diff --git a/packages/rocketchat-markdown/markdown.coffee b/packages/rocketchat-markdown/markdown.coffee
index 5f73fbce527..bc2de0b130b 100644
--- a/packages/rocketchat-markdown/markdown.coffee
+++ b/packages/rocketchat-markdown/markdown.coffee
@@ -11,10 +11,10 @@ class Markdown
 			msg = message.html
 
 			# Process MD like for strong, italic and strike
-			msg = msg.replace(/(\ |_|\~|\`|^)\*([^*]+)\*(\ |_|\~|\`|$)/gm, '$1<span class="copyonly">*</span><strong>$2</strong><span class="copyonly">*</span>$3')
-			msg = msg.replace(/(\ |\*|\~|\`|>|^)\_([^_]+)\_(\ |\*|\~|\`|<|$)/gm, '$1<span class="copyonly">_</span><em>$2</em><span class="copyonly">_</span>$3')
-			msg = msg.replace(/(\ |\*|_|\~|>|^)\`([^`]+)\`(\ |\*|\,|\.|_|\~|<|$)/gm, '$1<span class="copyonly">`</span><code class="inline">$2</code><span class="copyonly">`</span>$3')
-			msg = msg.replace(/(\ |\*|_|\`|>|^)\~{1,2}([^~]+)\~{1,2}(\ |\*|_|\`|<|$)/gm, '$1<span class="copyonly">~</span><strike>$2</strike><span class="copyonly">~</span>$3')
+			msg = msg.replace(/(^|&gt;|[ >_*~])\`([^`]+)\`([<_*~]|\B|\b|$)/gm, '$1<span class="copyonly">`</span><code class="inline">$2</code><span class="copyonly">`</span>$3')
+			msg = msg.replace(/(^|&gt;|[ >_~`])\*([^*]+)\*([<_~`]|\B|\b|$)/gm, '$1<span class="copyonly">*</span><strong>$2</strong><span class="copyonly">*</span>$3')
+			msg = msg.replace(/(^|&gt;|[ >*~`])\_([^_]+)\_([<*~`]|\B|\b|$)/gm, '$1<span class="copyonly">_</span><em>$2</em><span class="copyonly">_</span>$3')
+			msg = msg.replace(/(^|&gt;|[ >_*`])\~{1,2}([^~]+)\~{1,2}([<_*`]|\B|\b|$)/gm, '$1<span class="copyonly">~</span><strike>$2</strike><span class="copyonly">~</span>$3')
 			msg = msg.replace(/^&gt;(.*)$/gm, '<blockquote><span class="copyonly">&gt;</span>$1</blockquote>')
 			msg = msg.replace(/<\/blockquote>\n<blockquote>/gm, '</blockquote><blockquote>')