SMTP Outgoing Email broken in 10.9 + Missing User Library

[mhschmieder]

A few days ago, my outgoing email from Apple Mail desktop client stopped working, and has only on rare occasions sent an outgoing email since then, using SMTP through my internet provider (Astound) vs. my email provider (who I use for POPD or when doing outgoing email in Google Mail via the web browser). Astound says no problem at their end, so I did a search, and the whole world is having the same problem with SMTP in Apple Mail this past week.

Unfortunately I can't follow the advice given, due to another problem: my entire "username"/Library folder is missing (except on Time Machine Backup)! What gives? Is this no longer used in Mavericks vs. just the ones at the boot drive level and under the main System directory?

I think it may be because I had the Mail subfolder pointing to a separate drive as an alias. Maybe that caused the Mavericks update to erase the entire "username"/Library directory? But how is it finding my Mail directory (which it is) without the alias? Maybe it's hiding the directory from me, even after setting "show hidden files"?

I don't know which problem is scarier, but right now a lot is on the line due to not being able to send email. Especially if I'm responding to someone, cut/paste doesn't work (going to the web browser email) as it means my email might get marked as spam and not seen.

What should I do about the "username"/Library directory? Anything? I think I need to deal with that first, since the advice on the SMTP problem is to go to the Mail settings in that folder (though I can probably do the same thing on my non-system drive where I keep my Mail folder), and delete the preferences file as they suggest, then rebuild my email accounts (probably with new passwords).

[mhschmieder]

Although I still don't know why the "username"/Library directory disappeared (or went hidden) in its entirety, I have outgoing SMTP email working again from desktop Apple Mail, by allowing Yahoo to be my agent vs. Astound. I never use Yahoo email and only have an account for two Yahoo Groups that I log into twice a year, but at least it's serving a useful purpose now.

[mikehalloran]

The entire world? Big place. And the host says it's not their problem?

It's their problem.

I use Yahoo mail which occasionally has problems. My work uses Gmail which has its problems now and then - nearly all of us are on Macs, BTW and have updated to Maverics. We are not having email problems with Maverics.

[mhschmieder]

OK, good to know -- I'll stick with Yahoo for now as they don't seem to mind being my outgoing email agent.

I haven't followed all the Google hits yet, but there are many pages of people having SMTP problems this week with Apple Mail. So I think it's a combination of fault. But it's weird that the problems didn't start until a few days AFTER the Mavericks upgrade.

I'm still troubled by the missing user library directory, but am working overtime from home today and multi-tasking way too many things already as it is, to dig deep into that right now.

[MIDI Life Crisis]

No issues here. My Apple Mail program sends via my website host (GoDaddy) and I've not had one mail issue since installing ML.

It might be a case of: ever since I bought these new shoes my car has been acting up. My mechanic says it's not his problem and everybody (in the world... LOL) who bought these shoes has the same problem!

It's possible, but what is suspect is that it took a few days to appear. That would indicate a problem in the server side, as mentioned earlier.

As a test, you might want to log in as a new user acct. on the Mac and create the mail settings from scratch. Just a thought and a little inane attempt at humor. Sorry about that.

[Gravity Jim]

Also here, Mavericks and the new version of Mail have not caused any problem with my servers (at Dreamhost). Outgoing mail is A-OK.

[bayswater]

Same here. I have mail on four services, Apple, several accounts associated with a hosted domain, Gmail, and my ADSL provider. All transferred from 10.8 and worked with no hiccups.

(Both Library(s) are still there and still visible.)

[mikehalloran]

You are assuming that the error message is accurate. This is often the same error I see when the Yahoo SMTP server has issues about once or twice a year.

Being a paid subscriber, I get ticked and start thinking I should host my domain somewhere else. Then they fix the problem and everything works and the priority level drops to nil.

The biggest gmail issue is with Pages 5 attachments. Gmail treats them as executables even when zipped (remember how easy it was to spread viri as executibles through Exchange?). The workaround is to export Pages as any other supported format - incl. Pages 4.3, Word or .pdf - before attaching to Gmail.

I use gmail exclusively at work and don't allow work to interfere with home email. For that reason, I use the browser window for my Gmail client which works nicely. Since we are Office and GoogleDocs based, Pages attachments are never an issue - even though none of us use our work issued PCs anymore in favor of Macs.

[mhschmieder]

I'm going to have to live with all these annoyances for awhile as the work pressure is accelerating even though it was already insane (ironically part of the reason for that is all the "surprises" we are finding -- on the verge of a release date -- with the past few weeks worth of updates from Microsoft, Apple, Oracle, and others).

One thing I'm noticing is that -- even after reverting back to my internet account settings only checking the boxes for mail and nothing else, and only for Yahoo and Google -- I get all sorts of keychain login boxes every few minutes or so, which really is getting in the way but I have to brush them away like flies right now as I have way too many P1's simultaneously on my plate.

If I find out anything useful of benefit to others, I'll post it here though.

[MIDI Life Crisis]

This might be helpful...

http://www.macworld.com/article/2059577 ... -tips.html

Gmail and OS X Mail trouble. I don’t have the space to go into the details here. Suffice it to say that, if you use Gmail with OS X’s Mail app in Mavericks, you may see long delays before your messages appear. You may similarly find that, after adjusting Gmail’s All Mail setting, your entire archive of messages on Gmail re-downloads to your Mac. This is presumably not what you wanted to happen. Joe Kissell, writing in TidBITS, has all the dirt on this and other conflicts between Gmail and Mail in Mavericks. A bit of good news: 9to5Mac reports that Apple is working on a Mail update that will fix this and several other issues.

[mhschmieder]

Well, I reviewed all of that for the second time, and found nothing pertinent to my situation, which is not consistent from day to day or even within a given session. I'll just have to hope they fix it soon in an update.

As annoying as it is (now I can't send outgoing email via Yahoo either so have to resort to cut/paste of downloaded POPD messages to reply via Google Webmail), it does't hold a candle to the horror show that has been my life this week, working 18 hour days to try to (unsuccessfully) fix problems caused by the Windows 8.1 update (work-related; I don't use Windows for serious audio production duties ). I canceled next week's vacation because of it.

[mikehalloran]

There was an update to Mail yesterday. O didn't see a notification but when I opened the App store, it was there.

Experience is telling me that it is a problem with your host site, however.

[MIDI Life Crisis]

I still see a problem when trying to sort or even select a column in the " Get Info" mail window that results from selecting the little gear in the bottom left of the main mail viewer. The new update didn't address this and my post on Apple Discussions remains unanswered. Not a big deal as I only use it to check on older accounts to make sure a client from years ago hasn't emailed me on my previous email address. Still, when there are 40 or 50 emailed in there, it would be nice to sort them to scan them faster.

But as far as the o/p problem, I'm not seeing any issues in that regard.

[nick danger]

Mail is working OK, but one quirk is that in "mail activity" it shows multiple pieces of incoming/outgoing mail that doesn't correspond at all to actual activity.

[MIDI Life Crisis]

I see that too. One message coming in might show 5 coming in. One going out shows 2 or 3 going out. I suspect it's counting data packets.