diff --git a/lib/marked.js b/lib/marked.js
index 51c7c2ac06..8046be6fb7 100644
--- a/lib/marked.js
+++ b/lib/marked.js
@@ -606,7 +606,7 @@ inline.pedantic = merge({}, inline.normal, {
 inline.gfm = merge({}, inline.normal, {
   escape: edit(inline.escape).replace('])', '~|])').getRegex(),
   _extended_email: /[A-Za-z0-9._+-]+(@)[a-zA-Z0-9-_]+(?:\.[a-zA-Z0-9-_]*[a-zA-Z0-9])+(?![-_])/,
-  url: /^((?:ftp|https?):\/\/|www\.)(?:[a-zA-Z0-9\-]+\.?)+[^\s<]*|^email/,
+  url: /^((?:ftp|https?):\/\/|www\.)(?:[a-zA-Z0-9\-]+\.?)+[^\s<]*|^email/i,
   _backpedal: /(?:[^?!.,:;*_~()&]+|\([^)]*\)|&(?![a-zA-Z0-9]+;$)|[?!.,:;*_~)]+(?!$))+/,
   del: /^~+(?=\S)([\s\S]*?\S)~+/,
   text: edit(inline.text)
@@ -647,6 +647,7 @@ function InlineLexer(links, options) {
   } else if (this.options.gfm) {
     if (this.options.breaks) {
       this.rules = inline.breaks;
+      this.rules.url = new RegExp(this.rules.url.source, 'i');
     } else {
       this.rules = inline.gfm;
     }
diff --git a/test/unit/marked-spec.js b/test/unit/marked-spec.js
index 97789afe09..cdb897488c 100644
--- a/test/unit/marked-spec.js
+++ b/test/unit/marked-spec.js
@@ -25,3 +25,13 @@ describe('Test paragraph token type', function () {
     expect(tokens[7].type).toBe('text');
   });
 });
+
+describe('Test url token type', function () {
+  it('should use the "url" type', function () {
+    const md = 'HtTps://www.testsite.com';
+
+    const tokens = marked.lexer(md);
+
+    expect(tokens[0].type).toBe('url');
+  });
+});