Some WordPress plugins that protect your login page may be the culprit. Try disabling them to see if Chrome prompts to save the login. Don’t forget to re-enable them after you’ve managed to save your password in Chrome.
When I upload file attachment larger than ~1mb to Gmail using the Chrome web browser (v18.0.1025.33-r122015 google-chrome-beta on Ubuntu 11.10), the uploading will always fail after a while and Gmail will retry, resulting in an infinite loop to attach the same file.
Workaround: Use Firefox to attach such larger file attachments in Gmail. It works for me on the first try with Firefox 10.0.2.
Question: How to find out what contents on a HTTPS page is retrieved using HTTP, i.e. unencrypted in transit and thus open to sniffing?
Answer: Use Google Chrome web browser’s Developer Tools. Look under “Console” and you’ll see lines that look like this:
The page at https://www.example.com displayed insecure content from http://feeds.feedburner.com/notsecure.