SMTP Outgoing Email broken in 10.9 + Missing User Library

[mhschmieder]

I haven't really had time to follow up on this. Behaviour is chaotic and unpredictable. I've given up 100% on Astound for outgoing email and settled on Yahoo (which I don't really use), but still get into these weird situations where it either starts asking me to login every five minutes, or won't send saying everything (including Yahoo) is off-line. It's completely unpredictable and random so I just don't have the energy or time to try to figure the situation out as it isn't persistent; usually things are fine now.

[MIDI Life Crisis]

Going o/t here. Updated my wife's MBP from SL to Mavericks today. Now when you delete mail on the iPhone it deletes on the Yahoo server and visa versa. Move a message on the server to the trash and it moved to the trash on the iPhone. Move it to the inbox on the server and it moves to the inbox on the iPhone.

Others report similar and identical problems all around Apple discussions. No solution. Tested on my yahoo acct (I don't use it except in connection with my ATT service) and get the same results on my iPhone and the Yahoo server. Like iCloud sync but mail is not checked as bring thru iCloud and I thought that was only thru iCloud mail, not other servers.

Very disconcerting to say the least. Not getting the same issues with my servers on GoDaddy. Again, all was fine in SL earlier but now it's really kind of strange and clearly a Mac OS issue some report as of Lion.

[bayswater]

Sounds like your mail protocol has changed to IMAP. That's how IMAP works. I think it's the default for iCloud email.

[MIDI Life Crisis]

That sounds right. But that's strange since we didn't change the POP to IMAP. I guess it was always IMAP but the OS never really worked that way until the post SL world. I'll see if POP is available on the ATT server. Thanks for the suggestion.

[bayswater]

That sounds right. But that's strange since we didn't change the POP to IMAP.

I've heard something about iCloud forcing the issue. Syncing mail across devices doesn't really work with POP. I've turned iCloud mail syncing off, and then I use IMAP on mail accounts where I want it to sync. IIRC, the Apple mail accounts themselves can only be IMAP. From Apple support "iCloud Mail uses the IMAP and SMTP standards supported by most modern email apps. iCloud does not support POP."

[mikehalloran]

Hmmmmm....

I refuse to allow email on my iPhone so I guess that I am in the minority. I do have my Yahoo! email on my iPad, however. Also I do know the mail protocols since I use to do pre-sales support for a TCP/IP tools company.

POP downloads email to your computer while iMap controls the server. You can set up your Mac to use POP with your Yahoo! mail account. I have always had mine this way.

The key is to never delete email from your phone. Since it's not on the phone, you are not using memory. Once I learned to do that with my iPad, there was no longer an issue.

[bayswater]

I refuse to allow email on my iPhone

Why is that? Is there some serious vulnerability?

[mikehalloran]

I refuse to allow email on my iPhone

Why is that? Is there some serious vulnerability?

Not that I know of.

It's a personal preference. I do not wish to be tethered to the rest of the world when I am away from my computer. No email on my phone. No Facebook or anything like it either. It's bad enough that my work requires me to have a cell phone. I tolerate texting but don't use it for conversation - it has its place but if you want to talk, call. I can't imagine ever using a Twitter account. I like a little bit of privacy.

Because of my handicap, I work from an easy chair a lot. So my work phone forwards to my cell and can do quite a bit with my iPad. I appreciate technology but don't wish to be married to it any more than I am.

In a former job, one of the things I used to teach in time management seminars was to dedicate time to email and not to allow it to interrupt other activities. On that subject, I practice what I preach.

[bayswater]

It's a personal preference. I do not wish to be tethered to the rest of the world when I am away from my computer. No email on my phone. No Facebook or anything like it either. It's bad enough that my work requires me to have a cell phone.

I know what you mean. I had a boss who gave me a blackberry so he could contact me 7/24. For that reason I have email retrieval set up as a manual operation on my iPhone.

[mhschmieder]

The new Mavericks update from a few days ago was supposed to primarily address Apple Mail issues. I have seen no improvement at my end, and possibly things have gotten worse in terms of messages neither getting through nor reporting errors.

[MIDI Life Crisis]

I doesn't fix the gmail problem.

[mhschmieder]

There's been a huge improvement in Apple Mail performance and behavior on my machine in the past week, which makes me think the main problem was my internet provider (Astound) in spite of them insisting they had seen no compatibility issues with Mavericks. It seems likely they fixed problems at their end once they had more time to look at things in detail.

I still prefer the old behavior of logging into email directly, and once per session, vs. having to use my keychain login instead and having it popup for another login every now and then (though much less frequently than before; now it seems tied in with some timeout period vs. requiring a re-login every time I do anything on my system such as open a browser tab). It's just a security issue in my view; I would rather not have my keychain potentially compromised.

I was starting to think the flakiness might have been a result of having had to move my mail folder to another internal drive with an alias assigned to it, due to Mavericks pushing my SSD system drive 10 GB or so closer to its limit and thus almost constantly being a bottleneck even with mild browser use due to Safari's huge caching requirements now. Mavericks in general is about 4x as hungry as the Snow Leopard was.

I'll probably have to look at SSD upgrades in the next month; hopefully transferring my boot drive is not a complicated task when it's an SSD as the one I have is using the second media drive bay vs. an internal IDE drive bay.

[mhschmieder]

I think I finally figured out my on-again-off-again email problem with outgoing email refusing to send or being spurious, and all the annoying alert boxes requiring me to login constantly and to switch between Astound and Yahoo as the outgoing email service (separate from my incoming email service and/or email address): VPN's!

I am working from home today for the first time in a few weeks due to the company's end-of-year furlough, and this is the first time in that period that I have had the outgoing email problem, so for the first time I put two and two together, logged out of my VPN connection, and voila, email is working 100% again!

I can't claim to know why this is the case, but apparently something changed in Mavericks such that have an active VPN connection has a side effect on Apple Mail when it tries to use SMTP for outgoing email from the desktop, even though only the piped connections to external computers should be affected by the VPN login.

[mikehalloran]

I would look at all the new security settings. I had the exact issue when I updated from OS 10.4 to 10.5. Fortunately for me, my company no longer required me to use the VPN in 2010 so I've not been bothered by it since.

[mhschmieder]

Although I've done no recent updates, suddenly today I'm having outgoing email problems again, and this time with both Astound and Yahoo.

The only way to get a message to send is to turn off my Canon MG6320 printer and do a full power cycle of the MacPro. Nothing else works.

So, this means not only can I not send email if logged into work, but I can't turn my printer on at any point in a session or I lose the ability to send email to anyway except via the browser.