diff --git a/changelogs/unreleased/sh-fix-issue-52009.yml b/changelogs/unreleased/sh-fix-issue-52009.yml
new file mode 100644
index 0000000000000000000000000000000000000000..fc22a58a66aa4ccd5694e553d4e468362acd7ebe
--- /dev/null
+++ b/changelogs/unreleased/sh-fix-issue-52009.yml
@@ -0,0 +1,5 @@
+---
+title: Prevent Error 500s with invalid relative links
+merge_request: 22001
+author:
+type: fixed
diff --git a/lib/banzai/filter/relative_link_filter.rb b/lib/banzai/filter/relative_link_filter.rb
index 8e838d04badfe11c46ba6071723861849a62ae5d..7acbc933adcb4df77f56a4a9de056e14a019298e 100644
--- a/lib/banzai/filter/relative_link_filter.rb
+++ b/lib/banzai/filter/relative_link_filter.rb
@@ -60,7 +60,11 @@ module Banzai
           path_parts.unshift(relative_url_root, project.full_path)
         end
 
-        path = Addressable::URI.escape(File.join(*path_parts))
+        begin
+          path = Addressable::URI.escape(File.join(*path_parts))
+        rescue Addressable::URI::InvalidURIError
+          return
+        end
 
         html_attr.value =
           if context[:only_path]
diff --git a/spec/lib/banzai/filter/relative_link_filter_spec.rb b/spec/lib/banzai/filter/relative_link_filter_spec.rb
index ba8dc68ceda22839541b813c9e1cf5c7a963d036..ed1ebe9ebf6a69793454313fcb1ab089300b8356 100644
--- a/spec/lib/banzai/filter/relative_link_filter_spec.rb
+++ b/spec/lib/banzai/filter/relative_link_filter_spec.rb
@@ -83,6 +83,11 @@ describe Banzai::Filter::RelativeLinkFilter do
     expect { filter(act) }.not_to raise_error
   end
 
+  it 'does not raise an exception with a space in the path' do
+    act = link("/uploads/d18213acd3732630991986120e167e3d/Landscape_8.jpg  \nBut here's some more unexpected text :smile:)")
+    expect { filter(act) }.not_to raise_error
+  end
+
   it 'ignores ref if commit is passed' do
     doc = filter(link('non/existent.file'), commit: project.commit('empty-branch') )
     expect(doc.at_css('a')['href'])