diff --git a/app/services/web_hook_service.rb b/app/services/web_hook_service.rb
index 144d738dfd223..1fee8bfcd31b9 100644
--- a/app/services/web_hook_service.rb
+++ b/app/services/web_hook_service.rb
@@ -43,7 +43,7 @@ def execute
       http_status: response.code,
       message: response.to_s
     }
-  rescue SocketError, OpenSSL::SSL::SSLError, Errno::ECONNRESET, Errno::ECONNREFUSED, Errno::EHOSTUNREACH, Net::OpenTimeout, Net::ReadTimeout, Gitlab::HTTP::BlockedUrlError => e
+  rescue SocketError, OpenSSL::SSL::SSLError, Errno::ECONNRESET, Errno::ECONNREFUSED, Errno::EHOSTUNREACH, Net::OpenTimeout, Net::ReadTimeout, Gitlab::HTTP::BlockedUrlError, Gitlab::HTTP::RedirectionTooDeep => e
     log_execution(
       trigger: hook_name,
       url: hook.url,
diff --git a/changelogs/unreleased/52692-catch-redirect-loops.yml b/changelogs/unreleased/52692-catch-redirect-loops.yml
new file mode 100644
index 0000000000000..655124b8fb452
--- /dev/null
+++ b/changelogs/unreleased/52692-catch-redirect-loops.yml
@@ -0,0 +1,5 @@
+---
+title: Fix 500 error when testing webhooks with redirect loops
+merge_request: 22447
+author: Heinrich Lee Yu
+type: fixed
diff --git a/lib/gitlab/http.rb b/lib/gitlab/http.rb
index 9aca3b0fb264e..538b51c000854 100644
--- a/lib/gitlab/http.rb
+++ b/lib/gitlab/http.rb
@@ -5,9 +5,16 @@
 module Gitlab
   class HTTP
     BlockedUrlError = Class.new(StandardError)
+    RedirectionTooDeep = Class.new(StandardError)
 
     include HTTParty # rubocop:disable Gitlab/HTTParty
 
     connection_adapter ProxyHTTPConnectionAdapter
+
+    def self.perform_request(http_method, path, options, &block)
+      super
+    rescue HTTParty::RedirectionTooDeep
+      raise RedirectionTooDeep
+    end
   end
 end
diff --git a/spec/lib/gitlab/http_spec.rb b/spec/lib/gitlab/http_spec.rb
index d0dadfa78da2b..6c37c157f5d1c 100644
--- a/spec/lib/gitlab/http_spec.rb
+++ b/spec/lib/gitlab/http_spec.rb
@@ -46,4 +46,30 @@
       end
     end
   end
+
+  describe 'handle redirect loops' do
+    before do
+      WebMock.stub_request(:any, "http://example.org").to_raise(HTTParty::RedirectionTooDeep.new("Redirection Too Deep"))
+    end
+
+    it 'handles GET requests' do
+      expect { described_class.get('http://example.org') }.to raise_error(Gitlab::HTTP::RedirectionTooDeep)
+    end
+
+    it 'handles POST requests' do
+      expect { described_class.post('http://example.org') }.to raise_error(Gitlab::HTTP::RedirectionTooDeep)
+    end
+
+    it 'handles PUT requests' do
+      expect { described_class.put('http://example.org') }.to raise_error(Gitlab::HTTP::RedirectionTooDeep)
+    end
+
+    it 'handles DELETE requests' do
+      expect { described_class.delete('http://example.org') }.to raise_error(Gitlab::HTTP::RedirectionTooDeep)
+    end
+
+    it 'handles HEAD requests' do
+      expect { described_class.head('http://example.org') }.to raise_error(Gitlab::HTTP::RedirectionTooDeep)
+    end
+  end
 end
diff --git a/spec/services/web_hook_service_spec.rb b/spec/services/web_hook_service_spec.rb
index 622e56e1da5a5..b1cc6d2eb838e 100644
--- a/spec/services/web_hook_service_spec.rb
+++ b/spec/services/web_hook_service_spec.rb
@@ -97,7 +97,7 @@
     end
 
     it 'handles exceptions' do
-      exceptions = [SocketError, OpenSSL::SSL::SSLError, Errno::ECONNRESET, Errno::ECONNREFUSED, Errno::EHOSTUNREACH, Net::OpenTimeout, Net::ReadTimeout, Gitlab::HTTP::BlockedUrlError]
+      exceptions = [SocketError, OpenSSL::SSL::SSLError, Errno::ECONNRESET, Errno::ECONNREFUSED, Errno::EHOSTUNREACH, Net::OpenTimeout, Net::ReadTimeout, Gitlab::HTTP::BlockedUrlError, Gitlab::HTTP::RedirectionTooDeep]
       exceptions.each do |exception_class|
         exception = exception_class.new('Exception message')