diff --git a/dist/showdown.js b/dist/showdown.js
index 8b7e44d..af4d5e3 100644
Binary files a/dist/showdown.js and b/dist/showdown.js differ
diff --git a/dist/showdown.js.map b/dist/showdown.js.map
index 31a0dc6..bbfc3eb 100644
Binary files a/dist/showdown.js.map and b/dist/showdown.js.map differ
diff --git a/dist/showdown.min.js b/dist/showdown.min.js
index dde4210..0f229ce 100644
Binary files a/dist/showdown.min.js and b/dist/showdown.min.js differ
diff --git a/dist/showdown.min.js.map b/dist/showdown.min.js.map
index 70c1a54..84fbe2a 100644
Binary files a/dist/showdown.min.js.map and b/dist/showdown.min.js.map differ
diff --git a/src/subParsers/autoLinks.js b/src/subParsers/autoLinks.js
index 4bf53e9..44ec9e4 100644
--- a/src/subParsers/autoLinks.js
+++ b/src/subParsers/autoLinks.js
@@ -6,8 +6,8 @@ showdown.subParser('autoLinks', function (text, options, globals) {
   var simpleURLRegex  = /\b(((https?|ftp|dict):\/\/|www\.)[^'">\s]+\.[^'">\s]+)()(?=\s|$)(?!["<>])/gi,
       simpleURLRegex2 = /\b(((https?|ftp|dict):\/\/|www\.)[^'">\s]+\.[^'">\s]+?)([.!?()]?)(?=\s|$)(?!["<>])/gi,
       delimUrlRegex   = /<(((https?|ftp|dict):\/\/|www\.)[^'">\s]+)>/gi,
-      simpleMailRegex = /(?:^|\s)([A-Za-z0-9!#$%&'*+-/=?^_`{|}~.]+@[-a-z0-9]+(\.[-a-z0-9]+)*\.[a-z]+)(?:$|\s)/gi,
-      delimMailRegex  = /<(?:mailto:)?([-.\w]+@[-a-z0-9]+(\.[-a-z0-9]+)*\.[a-z]+)>/gi;
+      simpleMailRegex = /(^|\s)(?:mailto:)?([A-Za-z0-9!#$%&'*+-/=?^_`{|}~.]+@[-a-z0-9]+(\.[-a-z0-9]+)*\.[a-z]+)(?=$|\s)/gmi,
+      delimMailRegex  = /<()(?:mailto:)?([-.\w]+@[-a-z0-9]+(\.[-a-z0-9]+)*\.[a-z]+)>/gi;
 
   text = text.replace(delimUrlRegex, replaceLink);
   text = text.replace(delimMailRegex, replaceMail);
@@ -35,8 +35,9 @@ showdown.subParser('autoLinks', function (text, options, globals) {
     return '<a href="' + link + '">' + lnkTxt + '</a>' + append;
   }
 
-  function replaceMail(wholeMatch, mail) {
+  function replaceMail(wholeMatch, b, mail) {
     var href = 'mailto:';
+    b = b || '';
     mail = showdown.subParser('unescapeSpecialChars')(mail);
     if (options.encodeEmails) {
       mail = showdown.helper.encodeEmailAddress(mail);
@@ -44,7 +45,7 @@ showdown.subParser('autoLinks', function (text, options, globals) {
     } else {
       href = href + mail;
     }
-    return '<a href="' + href + '">' + mail + '</a>';
+    return b + '<a href="' + href + '">' + mail + '</a>';
   }
 
   text = globals.converter._dispatch('autoLinks.after', text, options, globals);
diff --git a/test/features/#330.simplifiedAutoLink-drops-character-before-and-after-linked-mail.html b/test/features/#330.simplifiedAutoLink-drops-character-before-and-after-linked-mail.html
new file mode 100644
index 0000000..e82b0ba
--- /dev/null
+++ b/test/features/#330.simplifiedAutoLink-drops-character-before-and-after-linked-mail.html
@@ -0,0 +1 @@
+<p>Just an example <a href="mailto:info@example.com">info@example.com</a> ok?​</p>
diff --git a/test/features/#330.simplifiedAutoLink-drops-character-before-and-after-linked-mail.md b/test/features/#330.simplifiedAutoLink-drops-character-before-and-after-linked-mail.md
new file mode 100644
index 0000000..ceb08b1
--- /dev/null
+++ b/test/features/#330.simplifiedAutoLink-drops-character-before-and-after-linked-mail.md
@@ -0,0 +1 @@
+Just an example info@example.com ok?​
\ No newline at end of file
diff --git a/test/node/testsuite.features.js b/test/node/testsuite.features.js
index f2bccc0..505cafc 100644
--- a/test/node/testsuite.features.js
+++ b/test/node/testsuite.features.js
@@ -55,6 +55,8 @@ describe('makeHtml() features testsuite', function () {
       converter = new showdown.Converter({ghMentions: true});
     } else if (testsuite[i].name === 'disable-email-encoding') {
       converter = new showdown.Converter({encodeEmails: false});
+    } else if (testsuite[i].name === '#330.simplifiedAutoLink-drops-character-before-and-after-linked-mail') {
+      converter = new showdown.Converter({encodeEmails: false, simplifiedAutoLink: true});
     } else {
       converter = new showdown.Converter();
     }