diff --git a/lib/docs/core/doc.rb b/lib/docs/core/doc.rb
index 0b913ef6..4bdfcf15 100644
--- a/lib/docs/core/doc.rb
+++ b/lib/docs/core/doc.rb
@@ -223,13 +223,14 @@ module Docs
       end
 
       opts[:logger].debug("Fetching #{url}")
-      response = Request.run(url, { headers: headers })
+      response = Request.run(url, { connecttimeout: 15, headers: headers })
 
       if response.success?
         response.body
       else
-        opts[:logger].error("Couldn't fetch #{url} (response code #{response.code})")
-        nil
+        reason = response.timed_out? ? "Timed out while fetching #{url}" : "Couldn't fetch #{url} (response code #{response.code})"
+        opts[:logger].error(reason)
+        raise reason
       end
     end
 
diff --git a/lib/tasks/updates.thor b/lib/tasks/updates.thor
index 66134581..20ef20b2 100644
--- a/lib/tasks/updates.thor
+++ b/lib/tasks/updates.thor
@@ -72,9 +72,9 @@ class UpdatesCLI < Thor
   rescue NotImplementedError
     logger.warn("Couldn't check #{doc.name}, get_latest_version is not implemented")
     error_result(doc, '`get_latest_version` is not implemented')
-  rescue
-    logger.error("Error while checking #{doc.name}")
-    raise
+  rescue => error
+    logger.error("Error while checking #{doc.name}\n#{error.full_message.strip}")
+    error_result(doc, error.message.gsub(/'/, '`'))
   end
 
   def format_version(version)