diff --git a/app/src/components/composer-editor/link-plugins.jsx b/app/src/components/composer-editor/link-plugins.jsx
index 319e6ff5d..66886f741 100644
--- a/app/src/components/composer-editor/link-plugins.jsx
+++ b/app/src/components/composer-editor/link-plugins.jsx
@@ -22,6 +22,22 @@ function onPaste(event, change, editor) {
   }
 }
 
+function buildAutoReplaceHandler({ hrefPrefix = '' } = {}) {
+  return function(transform, e, matches) {
+    if (transform.value.activeMarks.find(m => m.type === LINK_TYPE))
+      return transform.insertText(TriggerKeyValues[e.key]);
+
+    const link = matches.before[0];
+    const mark = Mark.create({ type: LINK_TYPE, data: { href: hrefPrefix + matches.before[0] } });
+    return transform
+      .deleteBackward(link.length)
+      .addMark(mark)
+      .insertText(link)
+      .removeMark(mark)
+      .insertText(TriggerKeyValues[e.key]);
+  };
+}
+
 function renderMark({ mark, children, targetIsHTML }) {
   if (mark.type !== LINK_TYPE) {
     return;
@@ -121,21 +137,14 @@ export default [
       },
     },
   },
+  AutoReplace({
+    trigger: e => !!TriggerKeyValues[e.key],
+    before: RegExpUtils.emailRegex({ requireStartOrWhitespace: true, matchTailOfString: true }),
+    transform: buildAutoReplaceHandler({ hrefPrefix: 'mailto:' }),
+  }),
   AutoReplace({
     trigger: e => !!TriggerKeyValues[e.key],
     before: RegExpUtils.urlRegex({ matchTailOfString: true }),
-    transform: (transform, e, matches) => {
-      if (transform.value.activeMarks.find(m => m.type === LINK_TYPE))
-        return transform.insertText(TriggerKeyValues[e.key]);
-
-      const link = matches.before[0];
-      const mark = Mark.create({ type: LINK_TYPE, data: { href: matches.before[0] } });
-      return transform
-        .deleteBackward(link.length)
-        .addMark(mark)
-        .insertText(link)
-        .removeMark(mark)
-        .insertText(TriggerKeyValues[e.key]);
-    },
+    transform: buildAutoReplaceHandler(),
   }),
 ];
diff --git a/app/src/regexp-utils.es6 b/app/src/regexp-utils.es6
index 80c3047c6..a2669ce28 100644
--- a/app/src/regexp-utils.es6
+++ b/app/src/regexp-utils.es6
@@ -17,11 +17,22 @@ const RegExpUtils = {
   // See http://tools.ietf.org/html/rfc5322#section-3.4 and
   // https://tools.ietf.org/html/rfc6531 and
   // https://en.wikipedia.org/wiki/Email_address#Local_part
-  emailRegex() {
-    return new RegExp(
-      `([a-z.A-Z${UnicodeEmailChars}0-9!#$%&\\'*+\\-/=?^_\`{|}~]+@[A-Za-z${UnicodeEmailChars}0-9.-]+\\.[A-Za-z]{2,63})`,
-      'g'
-    );
+  emailRegex({ requireStartOrWhitespace, matchTailOfString } = {}) {
+    const parts = [
+      `(`,
+      `[a-z.A-Z${UnicodeEmailChars}0-9!#$%&\\'*+\\-/=?^_\`{|}~]+`,
+      '@',
+      `[A-Za-z${UnicodeEmailChars}0-9.-]+\\.[A-Za-z]{2,63}`,
+      `)`,
+    ];
+    if (requireStartOrWhitespace) {
+      parts.unshift('(?:^|\\s{1})');
+    }
+    if (matchTailOfString) {
+      parts.push('$');
+    }
+
+    return new RegExp(parts.join(''), 'g');
   },
 
   // http://stackoverflow.com/questions/16631571/javascript-regular-expression-detect-all-the-phone-number-from-the-page-source