diff --git a/server/plugin.go b/server/plugin.go
index 3808bf26..3441b856 100644
--- a/server/plugin.go
+++ b/server/plugin.go
@@ -60,14 +60,27 @@ func (p *Plugin) MessageWillBePosted(c *plugin.Context, post *model.Post) (*mode
 			return false
 		}
 
-		if textNode, ok := node.(*markdown.Text); ok {
-			startPos, endPos := textNode.Range.Position+offset, textNode.Range.End+offset
-			origText := postText[startPos:endPos]
+		origText := ""
+		startPos := 0
+		endPos := 0
+
+		if autolinkNode, ok := node.(*markdown.Autolink); ok {
+			startPos, endPos = autolinkNode.RawDestination.Position+offset, autolinkNode.RawDestination.End+offset
+			origText = postText[startPos:endPos]
+			if autolinkNode.Destination() != origText {
+				mlog.Error(fmt.Sprintf("Markdown autolink did not match range text, '%s' != '%s'", autolinkNode.Destination(), origText))
+				return true
+			}
+		} else if textNode, ok := node.(*markdown.Text); ok {
+			startPos, endPos = textNode.Range.Position+offset, textNode.Range.End+offset
+			origText = postText[startPos:endPos]
 			if textNode.Text != origText {
 				mlog.Error(fmt.Sprintf("Markdown text did not match range text, '%s' != '%s'", textNode.Text, origText))
 				return true
 			}
+		}
 
+		if origText != "" {
 			newText := origText
 			for _, l := range links {
 				newText = l.Replace(newText)
@@ -78,6 +91,7 @@ func (p *Plugin) MessageWillBePosted(c *plugin.Context, post *model.Post) (*mode
 				offset += len(newText) - len(origText)
 			}
 		}
+
 		return true
 	})
 	post.Message = postText
diff --git a/server/plugin_test.go b/server/plugin_test.go
index b7a5e2e6..3ec82fe5 100644
--- a/server/plugin_test.go
+++ b/server/plugin_test.go
@@ -43,6 +43,9 @@ func TestSpecialCases(t *testing.T) {
 	}, &Link{
 		Pattern:  "(Example)",
 		Template: "[Example](https://example.com)",
+	}, &Link{
+		Pattern:  "(https://mattermost.atlassian.net/browse/)(MM)(-)(?P<jira_id>\\d+)",
+		Template: "[MM-$jira_id](https://mattermost.atlassian.net/browse/MM-$jira_id)",
 	}, &Link{
 		Pattern:  "(foo!bar)",
 		Template: "fb",
@@ -160,16 +163,27 @@ func TestSpecialCases(t *testing.T) {
 		}, {
 			"foo!bar & foo!bar\nfoo!bar & foo!bar\nfoo!bar & foo!bar",
 			"fb & fb\nfb & fb\nfb & fb",
+		}, {
+			"https://mattermost.atlassian.net/browse/MM-12345",
+			"[MM-12345](https://mattermost.atlassian.net/browse/MM-12345)",
+		}, {
+			"Welcome https://mattermost.atlassian.net/browse/MM-12345",
+			"Welcome [MM-12345](https://mattermost.atlassian.net/browse/MM-12345)",
+		}, {
+			"text https://mattermost.atlassian.net/browse/MM-12345 other text",
+			"text [MM-12345](https://mattermost.atlassian.net/browse/MM-12345) other text",
 		},
 	}
 
 	for _, tt := range tests {
-		post := &model.Post{
-			Message: tt.inputMessage,
-		}
+		t.Run(tt.inputMessage, func(t *testing.T) {
+			post := &model.Post{
+				Message: tt.inputMessage,
+			}
 
-		rpost, _ := p.MessageWillBePosted(&plugin.Context{}, post)
+			rpost, _ := p.MessageWillBePosted(&plugin.Context{}, post)
 
-		assert.Equal(t, tt.expectedMessage, rpost.Message)
+			assert.Equal(t, tt.expectedMessage, rpost.Message)
+		})
 	}
 }