diff --git a/CHANGELOG.txt b/CHANGELOG.txt
index e48816fa00..dbfdd64193 100644
--- a/CHANGELOG.txt
+++ b/CHANGELOG.txt
@@ -13,6 +13,7 @@ Changelog
  * Update documentation (configuring Django for Wagtail) to contain all current settings options (Matt Westcott, LB (Ben Johnston))
  * Added `defer` flag to `PageQuerySet.specific` (Karl Hobley)
  * Snippets can now be deleted from the listing view (LB (Ben Johnston))
+ * Increased max length of redirect URL field to 255 (Michael Harrison)
  * Fix: Handle all exceptions from `Image.get_file_size` (Andrew Plummer)
  * Fix: Fix display of breadcrumbs in ModelAdmin (LB (Ben Johnston))
 
diff --git a/docs/releases/2.2.rst b/docs/releases/2.2.rst
index 2952aa5ef4..803da92d78 100644
--- a/docs/releases/2.2.rst
+++ b/docs/releases/2.2.rst
@@ -22,6 +22,7 @@ Other features
  * Update documentation (configuring Django for Wagtail) to contain all current settings options (Matt Westcott, LB (Ben Johnston))
  * Added ``defer`` flag to ``PageQuerySet.specific`` (Karl Hobley)
  * Snippets can now be deleted from the listing view (LB (Ben Johnston))
+ * Increased max length of redirect URL field to 255 (Michael Harrison)
 
 Bug fixes
 ~~~~~~~~~
diff --git a/wagtail/contrib/redirects/migrations/0006_redirect_increase_max_length.py b/wagtail/contrib/redirects/migrations/0006_redirect_increase_max_length.py
new file mode 100644
index 0000000000..bed3fc554a
--- /dev/null
+++ b/wagtail/contrib/redirects/migrations/0006_redirect_increase_max_length.py
@@ -0,0 +1,18 @@
+# Generated by Django 2.0.2 on 2018-06-06 18:00
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('wagtailredirects', '0005_capitalizeverbose'),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name='redirect',
+            name='redirect_link',
+            field=models.URLField(blank=True, max_length=255, verbose_name='redirect to any URL'),
+        ),
+    ]
diff --git a/wagtail/contrib/redirects/models.py b/wagtail/contrib/redirects/models.py
index f389e4ed8d..6897d144d3 100644
--- a/wagtail/contrib/redirects/models.py
+++ b/wagtail/contrib/redirects/models.py
@@ -24,7 +24,7 @@ class Redirect(models.Model):
         null=True, blank=True,
         on_delete=models.CASCADE
     )
-    redirect_link = models.URLField(verbose_name=_("redirect to any URL"), blank=True)
+    redirect_link = models.URLField(verbose_name=_("redirect to any URL"), blank=True, max_length=255)
 
     @property
     def title(self):
diff --git a/wagtail/contrib/redirects/tests.py b/wagtail/contrib/redirects/tests.py
index 15b6434907..4e9140a1e8 100644
--- a/wagtail/contrib/redirects/tests.py
+++ b/wagtail/contrib/redirects/tests.py
@@ -422,6 +422,23 @@ class TestRedirectsAddView(TestCase, WagtailTestUtils):
         redirects = models.Redirect.objects.filter(redirect_link='http://www.test.com/')
         self.assertEqual(redirects.count(), 1)
 
+    def test_add_long_redirect(self):
+        response = self.post({
+            'old_path': '/test',
+            'site': '',
+            'is_permanent': 'on',
+            'redirect_link': 'https://www.google.com/search?q=this+is+a+very+long+url+because+it+has+a+huge+search+term+appended+to+the+end+of+it+even+though+someone+should+really+not+be+doing+something+so+crazy+without+first+seeing+a+psychiatrist',
+        })
+
+        # Should redirect back to index
+        self.assertRedirects(response, reverse('wagtailredirects:index'))
+
+        # Check that the redirect was created
+        redirects = models.Redirect.objects.filter(old_path='/test')
+        self.assertEqual(redirects.count(), 1)
+        self.assertEqual(redirects.first().redirect_link, 'https://www.google.com/search?q=this+is+a+very+long+url+because+it+has+a+huge+search+term+appended+to+the+end+of+it+even+though+someone+should+really+not+be+doing+something+so+crazy+without+first+seeing+a+psychiatrist')
+        self.assertEqual(redirects.first().site, None)
+
 
 class TestRedirectsEditView(TestCase, WagtailTestUtils):
     def setUp(self):