diff --git a/app/models/topic_link.rb b/app/models/topic_link.rb
index 1770ea7ed48..6758689c712 100644
--- a/app/models/topic_link.rb
+++ b/app/models/topic_link.rb
@@ -386,7 +386,7 @@ end
 #  topic_id      :integer          not null
 #  post_id       :integer
 #  user_id       :integer          not null
-#  url           :string(500)      not null
+#  url           :string           not null
 #  domain        :string(100)      not null
 #  internal      :boolean          default(FALSE), not null
 #  link_topic_id :integer
diff --git a/db/post_migrate/20210525112226_remove_length_constrain_from_topic_link_url.rb b/db/post_migrate/20210525112226_remove_length_constrain_from_topic_link_url.rb
new file mode 100644
index 00000000000..f7d9c606f20
--- /dev/null
+++ b/db/post_migrate/20210525112226_remove_length_constrain_from_topic_link_url.rb
@@ -0,0 +1,11 @@
+# frozen_string_literal: true
+
+class RemoveLengthConstrainFromTopicLinkUrl < ActiveRecord::Migration[6.1]
+  def up
+    change_column :topic_links, :url, :string, null: false
+  end
+
+  def down
+    raise ActiveRecord::IrreversibleMigration
+  end
+end
diff --git a/spec/models/topic_link_spec.rb b/spec/models/topic_link_spec.rb
index b6f6f1c9790..6e52b74c231 100644
--- a/spec/models/topic_link_spec.rb
+++ b/spec/models/topic_link_spec.rb
@@ -201,6 +201,42 @@ describe TopicLink do
         expect(other_topic.reload.topic_links.where(link_post_id: linked_post.id)).to be_blank
 
       end
+
+      it 'truncates long links' do
+        SiteSetting.slug_generation_method = 'encoded'
+        long_title = "Καλημερα σε ολους και ολες" * 9 # 234 chars, but the encoded slug will be 1224 chars in length
+        other_topic = Fabricate(:topic, user: user, title: long_title)
+        expect(other_topic.slug.length).to be > TopicLink.max_url_length
+        other_topic.posts.create(user: user, raw: 'initial post')
+        other_topic_url = "http://#{test_uri.host}/t/#{other_topic.slug}/#{other_topic.id}"
+
+        post_with_link = topic.posts.create(user: user, raw: "Link to another topic: #{other_topic_url}")
+        TopicLink.extract_from(post_with_link)
+        topic.reload
+        link = topic.topic_links.first
+
+        expect(link.url.length).to eq(TopicLink.max_url_length)
+      end
+
+      it 'does not truncate reflection links' do
+        SiteSetting.slug_generation_method = 'encoded'
+        long_title = "Καλημερα σε ολους και ολες" * 9 # 234 chars, but the encoded slug will be 1224 chars in length
+        topic = Fabricate(:topic, user: user, title: long_title)
+        expect(topic.slug.length).to be > TopicLink.max_url_length
+        topic_url = "http://#{test_uri.host}/t/#{topic.slug}/#{topic.id}"
+
+        other_topic = Fabricate(:topic, user: user)
+        other_topic.posts.create(user: user, raw: 'initial post')
+        other_topic_url = "http://#{test_uri.host}/t/#{other_topic.slug}/#{other_topic.id}"
+
+        post_with_link = topic.posts.create(user: user, raw: "Link to another topic: #{other_topic_url}")
+        expect { TopicLink.extract_from(post_with_link) }.to_not raise_error
+
+        other_topic.reload
+        reflection_link = other_topic.topic_links.first
+        expect(reflection_link.url.length).to be > (TopicLink.max_url_length)
+        expect(reflection_link.url).to eq(topic_url)
+      end
     end
 
     context "link to a user on discourse" do