Sorry for the repetitive-looking post but all relevant ones are locked through inactivity. Recently Mail.app spontaneously lost the ability to send outgoing messages - even though I had checked and re-checked (and re-re-checked) that the account/passwords were correct, Apple Mail was unable to connect to the server. This has happened sporadically in the past, and seems to have come to stay this time. Then yesterday the problem spread to receiving emails – the entire account is now completely unable to communicate with the outside world, and Gmail servers in particular. 'The connection to the server ' on port 993 timed out.' Oddly, though, Mail.app is able to sync mail with my Microsoft Exchange account, so I don't think the app is defective.

I've tried editing the SMTP servers list. I've tried re-entering the password. I've tried changing the password to the 2-stage application-specific password. I've tried deleting Keychain passwords for and and re-entering them. Lastly - and this one is really fun - I tried deleting and reinstalling the account on Mail. I got halfway and now it won't recognise any connection to reinstall the account.

Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be sent. I've never had a mac before so I'm not super confident in playing around with it.

Other specs: OSX 10.8.4 Mail v.5.3 thedavemonster 9/10/2013, 8:54 น. After posting I found this thread () – pretty similar but nothing on it helps. Solutions offered on there: -- telnet 993 Trying 173.194.66.108. Telnet: connect to address: Operation timed out Trying 173.194.66.109.

Telnet: connect to address: Operation timed out Trying 2a00:1450:400c:c05::6c. Telnet: connect to address 2a00:1450:400c:c05::6c: No route to host telnet: Unable to connect to remote host --- 173.194.66.108 ping statistics --- 4 packets transmitted, 4 packets received, 0.0% packet loss round-trip min/avg/max/stddev = 29.980/30.675/32.179/0.877 ms --- 173.194.66.109 ping statistics --- 4 packets transmitted, 4 packets received, 0.0% packet loss round-trip min/avg/max/stddev = 27.695/27.948/28.378/0.260 ms wdurham 9/10/2013, 9:33 น. @wdurham I read through all of this in other feeds and on Google's help page (your ref) and then posted this discussion as nothing worked. I've tried UnlockCaptcha (whatever the hell that does; didn't seem to make a bit of difference), and all logging out of my clients has done for me is make me unable to log in and see the emails they'd downloaded before all of this crap began. Now I have even less access. I've even turned 2-step back off because all those extra passwords is just making troubleshooting even more complicated. Also, since posting yesterday, the native iOS mail clients on BOTH my iPhone and iPad have also stopped working.

It's slowly spreading, like Rise of the Machines crossed with The Birds over here. Throughout all of this the only reliable way to accessing my emails is via a web browser - thereby completely negating the whole point of clients existing in the first place. I this Google trying to force people to use their Mail app (which works) rather than the indigenous client built into iOS? Hsa account that works with quicken for mac. Is there a power play at work? What the £&@!

Is happening? Thedavemonster, 3:38 น.

Thanks for the ongoing help. Let's figure this out. I am using the Apple Mail client on a MacBook to access Gmail. I didn't previously use 2-step verification on any Google account, and the imap/smtp problems began whilst it was still deactivated. I activated it in the hope that a new, 'securer' password would help, but it didn't. So I turned it off again. On my MacBook: - I logged into web-based Gmail with no problem.

- I went to DisplayUnlockCaptcha & allowed access. - I then attempted to re-add my Gmail account on Mail.app and got: 'The Google IMAP server “” is not responding. Try checking the network connection, and that the server name is correct.

Otherwise, the server might be temporarily unavailable. If you continue, you might not be able to receive messages.' On my phone: - I logged into the separate native Gmail app to check; no problem. - I logged into Gmail on my phone using Safari; no problem. - I then attempted to log into my indigenous iOS Mail app and got: 'The mail server ' is not responding.