diff --git a/internal_packages/message-list/lib/autolinker.es6 b/internal_packages/message-list/lib/autolinker.es6
index 0c1284927..064d52c1e 100644
--- a/internal_packages/message-list/lib/autolinker.es6
+++ b/internal_packages/message-list/lib/autolinker.es6
@@ -1,5 +1,14 @@
 import {RegExpUtils, DOMUtils} from 'nylas-exports';
 
+function _matchesAnyRegexp(text, regexps) {
+  for (const excludeRegexp of regexps) {
+    if (excludeRegexp.test(text)) {
+      return true;
+    }
+  }
+  return false;
+}
+
 function _runOnTextNode(node, matchers) {
   if (node.parentElement) {
     const withinScript = node.parentElement.tagName === "SCRIPT";
@@ -12,20 +21,34 @@ function _runOnTextNode(node, matchers) {
   if (node.textContent.trim().length < 4) {
     return;
   }
-  for (const [prefix, regex] of matchers) {
+
+  let longest = null;
+  let longestLength = null;
+  for (const [prefix, regex, options = {}] of matchers) {
     regex.lastIndex = 0;
     const match = regex.exec(node.textContent);
     if (match !== null) {
-      const href = `${prefix}${match[0]}`;
-      const range = document.createRange();
-      range.setStart(node, match.index);
-      range.setEnd(node, match.index + match[0].length);
-      const aTag = DOMUtils.wrap(range, 'A');
-      aTag.href = href;
-      aTag.title = href;
-      return;
+      if (options.exclude && _matchesAnyRegexp(match[0], options.exclude)) {
+        continue;
+      }
+      if (match[0].length > longestLength) {
+        longest = [prefix, match];
+        longestLength = match[0].length;
+      }
     }
   }
+
+  if (longest) {
+    const [prefix, match] = longest;
+    const href = `${prefix}${match[0]}`;
+    const range = document.createRange();
+    range.setStart(node, match.index);
+    range.setEnd(node, match.index + match[0].length);
+    const aTag = DOMUtils.wrap(range, 'A');
+    aTag.href = href;
+    aTag.title = href;
+    return;
+  }
 }
 
 export function autolink(doc, {async} = {}) {
@@ -33,7 +56,11 @@ export function autolink(doc, {async} = {}) {
   // and ensure anything with an href has a title attribute.
   const textWalker = document.createTreeWalker(doc.body, NodeFilter.SHOW_TEXT);
   const matchers = [
-    ['mailto:', RegExpUtils.emailRegex()],
+    ['mailto:', RegExpUtils.emailRegex(), {
+      // Technically, gmail.com/bengotow@gmail.com is an email address. After
+      // matching, manully exclude any email that follows the .*[/?].*@ pattern.
+      exclude: [/\..*[\/|\?].*\@/],
+    }],
     ['tel:', RegExpUtils.phoneRegex()],
     ['', RegExpUtils.urlRegex({matchEntireString: false})],
   ];
diff --git a/internal_packages/message-list/spec/autolinker-fixtures/both-email-and-url-in.html b/internal_packages/message-list/spec/autolinker-fixtures/both-email-and-url-in.html
new file mode 100644
index 000000000..87e893b88
--- /dev/null
+++ b/internal_packages/message-list/spec/autolinker-fixtures/both-email-and-url-in.html
@@ -0,0 +1,4 @@
+To test this, send https://www.google.com/search?q=test@example.com or gmail.com?q=bengotow@gmail.com
+to yourself from a client that allows plaintext or html editing.
+
+What about gmail.com/bengotow@gmail.com - Oh man you're asking for trouble.
diff --git a/internal_packages/message-list/spec/autolinker-fixtures/both-email-and-url-out.html b/internal_packages/message-list/spec/autolinker-fixtures/both-email-and-url-out.html
new file mode 100644
index 000000000..51d7ebf17
--- /dev/null
+++ b/internal_packages/message-list/spec/autolinker-fixtures/both-email-and-url-out.html
@@ -0,0 +1,4 @@
+To test this, send <a href="https://www.google.com/search?q=test@example.com" title="https://www.google.com/search?q=test@example.com">https://www.google.com/search?q=test@example.com</a> or <a href="gmail.com?q=bengotow@gmail.com" title="gmail.com?q=bengotow@gmail.com">gmail.com?q=bengotow@gmail.com</a>
+to yourself from a client that allows plaintext or html editing.
+
+What about <a href="gmail.com/bengotow@gmail.com" title="gmail.com/bengotow@gmail.com">gmail.com/bengotow@gmail.com</a> - Oh man you're asking for trouble.
diff --git a/src/regexp-utils.coffee b/src/regexp-utils.coffee
index 4f3e744ff..3e0f7aba7 100644
--- a/src/regexp-utils.coffee
+++ b/src/regexp-utils.coffee
@@ -14,7 +14,7 @@ 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: -> new RegExp(/([a-z.A-Z0-9!#$%&'*+\-/=?^_`{|}~;:]+@[A-Za-z0-9.-]+\.[A-Za-z]{2,63})/g)
+  emailRegex: -> new RegExp(/([a-z.A-Z0-9!#$%&'*+\-/=?^_`{|}~;]+@[A-Za-z0-9.-]+\.[A-Za-z]{2,63})/g)
 
   # http://stackoverflow.com/questions/16631571/javascript-regular-expression-detect-all-the-phone-number-from-the-page-source
   # http://www.regexpal.com/?fam=94521