diff --git a/src/addons/webLinks/webLinks.test.ts b/src/addons/webLinks/webLinks.test.ts
index c84ee1a5ef..ce9b8b4421 100644
--- a/src/addons/webLinks/webLinks.test.ts
+++ b/src/addons/webLinks/webLinks.test.ts
@@ -39,4 +39,28 @@ describe('webLinks addon', () => {
 
     assert.equal(uri, 'http://foo.com/a~b#c~d?e~f');
   });
+
+  it('should allow : character in URI path', () => {
+    const term = new MockTerminal();
+    webLinks.webLinksInit(<any>term);
+
+    const row = '  http://foo.com/colon:test  ';
+
+    const match = row.match(term.regex);
+    const uri = match[term.options.matchIndex];
+
+    assert.equal(uri, 'http://foo.com/colon:test');
+  });
+
+  it('should not allow : character at the end of a URI path', () => {
+    const term = new MockTerminal();
+    webLinks.webLinksInit(<any>term);
+
+    const row = '  http://foo.com/colon:test:  ';
+
+    const match = row.match(term.regex);
+    const uri = match[term.options.matchIndex];
+
+    assert.equal(uri, 'http://foo.com/colon:test');
+  });
 });
diff --git a/src/addons/webLinks/webLinks.ts b/src/addons/webLinks/webLinks.ts
index a007bbd618..75d79104f3 100644
--- a/src/addons/webLinks/webLinks.ts
+++ b/src/addons/webLinks/webLinks.ts
@@ -14,7 +14,7 @@ const ipClause = '((\\d{1,3}\\.){3}\\d{1,3})';
 const localHostClause = '(localhost)';
 const portClause = '(:\\d{1,5})';
 const hostClause = '((' + domainBodyClause + '\\.' + tldClause + ')|' + ipClause + '|' + localHostClause + ')' + portClause + '?';
-const pathClause = '(\\/[\\/\\w\\.\\-%~]*)*';
+const pathClause = '(\\/[\\/\\w\\.\\-%~:]*)*([^:\\s])';
 const queryStringHashFragmentCharacterSet = '[0-9\\w\\[\\]\\(\\)\\/\\?\\!#@$%&\'*+,:;~\\=\\.\\-]*';
 const queryStringClause = '(\\?' + queryStringHashFragmentCharacterSet + ')?';
 const hashFragmentClause = '(#' + queryStringHashFragmentCharacterSet + ')?';