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 Post Posted: Fri Feb 02, 2018 8:07 pm 
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Joined: Tue Oct 17, 2017 11:09 am
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I have had recurring problems with sending mail under Sierra, to which I have recently upgraded.

Just for the moment, I wish to know if anyone had, or is having, such an issue: not being able to reliably connect to an outgoing (smtp) server. Days go by without a problem (messages are sent), and then I cannot send messages. I manage to overcome the issue, but it's only temporarily. One computer had the problem, but no longer seems to; one computer has this recurring situation.

Happy to give much more specific info if asked for it.


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 Post Posted: Fri Feb 02, 2018 9:44 pm 
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Joined: Thu Jun 19, 2014 10:23 pm
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Hi Gail,

No problem in 10.12 here, but in the pst this intermittent thing hs generally been duplicate keychains with one having n older PW in it.


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 Post Posted: Sat Feb 03, 2018 9:50 am 
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I did change my password for this account (a Gmail one) quite some time ago however, and there were some duplicates in my Keychain app. I trashed whatever seemed okay to trash. I guess that if something needs to be generated anew, it will be.

The problem has been awful and frustrating, but the worst part of it is: whenever the issue occurs, the actual settings in the Google outgoing server portion of Mail’s preferences get changed!! This changing of the settings has been driving me bonkers. I can see where having duplicate files could cause this.

There are also items in Keychain called Google Authentication Token, and I also have more than one of those. I didn't remove either one; they both have the same date, from a long time ago. I didn't feel so confident in trashing those, but I can do it later if needed. I also don't know if that token has to do with the outgoing mail server.

Thanks so much :D for this hint of yours. Only time will tell (a week at most, if it ”keeps to schedule”) if it has done the trick. In the moment, I am able to send mails, but that seems to be the "cycle" in which I am. Trashing the Keychain items hasn't caused any problems.


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 Post Posted: Sun Feb 04, 2018 1:27 am 
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OK, keep us posted, I never have figgured out why or when Mail decides to use which Keychain entry, then to complicate things Apple uses a lot more consistent Caches now than before.


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 Post Posted: Sun Feb 04, 2018 9:36 pm 
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Joined: Thu Oct 07, 2010 4:36 pm
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Location: Warrington
I'm using Gmail on Sierra via Apple Mail. Not having any problems here.

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 Post Posted: Mon Feb 05, 2018 10:08 pm 
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No good. Back to square one. Again, cannot send mails. Need to fiddle some more, beyond the fiddling that (only temporarily) solves the problem. Need to stay sane. Difficult.


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 Post Posted: Fri Feb 16, 2018 4:51 pm 
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So I did some more fiddling, which may or my not have had to do with Keychain. What I mean by that is my fiddling may have indirectly removed some offending/conflicting files there. But this time, I did not fiddle within Keychain.
And I have been able to send messages without incident for a week now. A week is not really long enough to be able to say, ”mission accomplished”, but I’m cautiously hopeful.
Thanks, BDAqua, for your input.

But now a new problem. See the topic ”Apple Mail quits upon launch”.
Related? I don’t think so.


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