diff --git a/Library/Homebrew/utils/curl.rb b/Library/Homebrew/utils/curl.rb
index f6d7cbea7..0a2560965 100644
--- a/Library/Homebrew/utils/curl.rb
+++ b/Library/Homebrew/utils/curl.rb
@@ -85,7 +85,7 @@ module Utils
 
       return result if result.success? || !args.exclude?("--http1.1")
 
-      raise Timeout::Error, result.stderr.chomp if result.status.exitstatus == 28
+      raise Timeout::Error, result.stderr.lines.last.chomp if timeout && result.status.exitstatus == 28
 
       # Error in the HTTP2 framing layer
       if result.status.exitstatus == 16
@@ -176,9 +176,12 @@ module Utils
       hash_needed = false
       if url != secure_url
         user_agents.each do |user_agent|
-          secure_details =
+          secure_details = begin
             curl_http_content_headers_and_checksum(secure_url, specs: specs, hash_needed: true,
                                                    user_agent: user_agent)
+          rescue Timeout::Error
+            next
+          end
 
           next unless http_status_ok?(secure_details[:status])