If you had been following my blog for a while you would know that I use my desktop to store all the files and use the other devices to access them over Wi-Fi. Now that I do not have a tablet, I use the MacBook for all my media consumption tasks, when my wife is using the desktop PC.
To connect to the desktop PC, I have to go use Connect to Server option in Finder. You would see a dialog box like this.
But I was having this problem. OSX never remembers the login credentials to my Desktop PC despite commanding it to store them in KeyChain. I have done this several times and it never seemed to remember them. Entering the username and password is a pain because they are same as Microsoft Account's: they are long!
Today I finally wanted to get deep into this issue.
I opened KeyChain app and checked if my login details are really saved in there. I saw two entries and thinking that they were conflicting each other, I deleted one. Then just to make sure that everything is in order, I opened the only one remaining. And then I could figure out what really was wrong.
The address which was stored in the KeyChain entry was not the same address as I would usually input. Instead of saving smb://desktop/, it had saved smb://desktop/documents/. So if I used smb://desktop/documents/ as the server to connect to, it would have automatically logged me in. But since the address was different, it couldn't. Kind of stupid, if you ask me. I mean, why wouldn't it even try?
So I changed the address in the KeyChain entry to smb://desktop/ and it logged me in automatically when I tried next time. Victory!