diff --git a/app/logical/danbooru/http.rb b/app/logical/danbooru/http.rb
index 43530522e..6147218f7 100644
--- a/app/logical/danbooru/http.rb
+++ b/app/logical/danbooru/http.rb
@@ -120,11 +120,17 @@ module Danbooru
 
     def request(method, url, **options)
       http.send(method, url, **options)
+    rescue OpenSSL::SSL::SSLError
+      fake_response(590, "")
     rescue ValidatingSocket::ProhibitedIpError
-      fake_response(597, "")
+      fake_response(591, "")
     rescue HTTP::Redirector::TooManyRedirectsError
-      fake_response(598, "")
+      fake_response(596, "")
     rescue HTTP::TimeoutError
+      fake_response(597, "")
+    rescue HTTP::ConnectionError
+      fake_response(598, "")
+    rescue HTTP::Error
       fake_response(599, "")
     end
 
diff --git a/test/unit/danbooru_http_test.rb b/test/unit/danbooru_http_test.rb
index 08ad71f64..a981bc0ea 100644
--- a/test/unit/danbooru_http_test.rb
+++ b/test/unit/danbooru_http_test.rb
@@ -19,21 +19,31 @@ class DanbooruHttpTest < ActiveSupport::TestCase
       should "fail if redirected too many times" do
         skip "Skipping test (https://github.com/postmanlabs/httpbin/issues/617)"
         response = Danbooru::Http.get("https://httpbin.org/absolute-redirect/10")
-        assert_equal(598, response.status)
+        assert_equal(596, response.status)
       end
 
       should "fail if the request takes too long to connect" do
         response = Danbooru::Http.timeout(1).get("https://httpbin.org/delay/5")
-        assert_equal(599, response.status)
+        assert_equal(597, response.status)
       end
 
       should "fail if the request takes too long to download" do
-        # XXX should return status 599 instead
+        # XXX should return status 597 instead
         assert_raises(HTTP::TimeoutError) do
           response = Danbooru::Http.timeout(1).get("https://httpbin.org/drip?duration=10&numbytes=10").flush
         end
       end
 
+      should "return a 5xx error if the domain can't be resolved" do
+        response = Danbooru::Http.get("http://doesnotexist.donmai.us")
+        assert_equal(598, response.status)
+      end
+
+      should "return a 5xx error if the SSL certificate is expired" do
+        response = Danbooru::Http.get("https://expired.badssl.com")
+        assert_equal(590, response.status)
+      end
+
       should "automatically decompress gzipped responses" do
         response = Danbooru::Http.get("https://httpbin.org/gzip")
         assert_equal(200, response.status)