Update 10/3/13 I’ve been getting a higher and higher number of people asking about Safari flat out refusing to save passwords on certain sites where it used to.
A bit of research made me realize what I should have known: Safari 6 and up will respect a website requesting that certain fields not be autocompleted (such as PayPal and Yahoo). There’s not much you can do about it within Safari, although you could use a third party password manager such as 1Password or a free extension (that link will download it) that would make Safari ignore the autocomplete request.
Update: I’m getting a surprising number of people from around the planet hitting this article, searching for things like ‘Safari isn’t saving password’, ‘Mac keychain’ and ‘why oh why am I always being asked for my keychain password someone help me please’. Anyway, if the article doesn’t answer the question, don’t hesitate to drop a question in the comments.
Your Mac, much like, say, a sheepdog, is supposed to make your life easier by fulfilling your commands. And much like a sheepdog, when you give it a clear, distinct command, and it lopes off into the sunset ignoring it completely, it’s apt to raise your blood pressure.
Just to take an example: lets say you’re doing your daily check in on your webmail, and lets say you’re using yahoo mail. You cheerfully plug in your username and password, and when Safari asks you ‘Hey, would you like to save this password for later?’ you say ‘yes.’
The next day, you happily surf back to Yahoo webmail, innocently expecting that there will be no more password typing for you (after all, typing 123456 can get a bit old).
As an unusually perspicacious individual (evidenced by you reading this blog), you’ve probably already guessed the punchline: not only has your Mac NOT remembered the password, but it pretty much refuses to do it even after you go through the entire denial, rage, and piteous begging stages of troubleshooting.
What is up?