diff --git a/spacy/tests/tokenizer/test_urls.py b/spacy/tests/tokenizer/test_urls.py
index 5d0654d50..1a964d5e5 100644
--- a/spacy/tests/tokenizer/test_urls.py
+++ b/spacy/tests/tokenizer/test_urls.py
@@ -2,8 +2,7 @@ from __future__ import unicode_literals
 
 import pytest
 
-
-@pytest.mark.parametrize("text", [
+URLS = [
     u"http://www.nytimes.com/2016/04/20/us/politics/new-york-primary-preview.html?hp&action=click&pgtype=Homepage&clickSource=story-heading&module=a-lede-package-region&region=top-news&WT.nav=top-news&_r=0",
     u"www.google.com?q=google",
     u"google.com",
@@ -13,7 +12,66 @@ import pytest
     u"http://www.example.com/wpstyle/?bar=baz&inga=42&quux",
     u"mailto:foo.bar@baz.com",
     u"mailto:foo-bar@baz-co.com"
-])
+]
+
+# Punctuation we want to check is split away before the URL
+PREFIXES = [
+    "(", '"', "...", ":", "<", ">", ")"
+]
+
+# Punctuation we want to check is split away after the URL
+SUFFIXES = [
+    "(", '"', "...", ":", "<", ">"]
+
+@pytest.mark.parametrize("text", URLS)
 def test_simple_url(en_tokenizer, text):
     tokens = en_tokenizer(text)
     assert tokens[0].orth_ == text
+    assert len(tokens) == 1
+
+
+@pytest.mark.parametrize("prefix", PREFIXES)
+@pytest.mark.parametrize("url", URLS)
+def test_prefixed_url(en_tokenizer, prefix, url):
+    tokens = en_tokenizer(prefix + url)
+    assert tokens[0].text == prefix
+    assert tokens[1].text == url
+    assert len(tokens) == 2
+    
+@pytest.mark.parametrize("suffix", SUFFIXES)
+@pytest.mark.parametrize("url", URLS)
+def test_prefixed_url(en_tokenizer, suffix, url):
+    tokens = en_tokenizer(url + suffix)
+    assert tokens[1].text == suffix
+    assert tokens[0].text == url
+    assert len(tokens) == 2
+    
+@pytest.mark.parametrize("prefix", PREFIXES)
+@pytest.mark.parametrize("suffix", SUFFIXES)
+@pytest.mark.parametrize("url", URLS)
+def test_surround_url(en_tokenizer, prefix, suffix, url):
+    tokens = en_tokenizer(prefix + url + suffix)
+    assert tokens[0].text == prefix
+    assert tokens[1].text == url
+    assert tokens[2].text == suffix
+    assert len(tokens) == 3
+    
+@pytest.mark.parametrize("prefix1", PREFIXES)
+@pytest.mark.parametrize("prefix2", PREFIXES)
+@pytest.mark.parametrize("url", URLS)
+def test_two_prefix_url(en_tokenizer, prefix1, prefix2, url):
+    tokens = en_tokenizer(prefix1 + prefix2 + url)
+    assert tokens[0].text == prefix1
+    assert tokens[1].text == prefix2
+    assert tokens[2].text == url
+    assert len(tokens) == 3
+    
+@pytest.mark.parametrize("suffix1", SUFFIXES)
+@pytest.mark.parametrize("suffix2", SUFFIXES)
+@pytest.mark.parametrize("url", URLS)
+def test_two_prefix_url(en_tokenizer, suffix1, suffix2, url):
+    tokens = en_tokenizer(url + suffix1 + suffix2)
+    assert tokens[0].text == url
+    assert tokens[1].text == suffix1
+    assert tokens[2].text == suffix2
+    assert len(tokens) == 3