Problem with SMTP servers that disappear

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Level 1

7 points

Problem with SMTP servers that disappear

I recently upgraded to Sierra official release.

Since then, I can't send no more mail.

I have a special setup in Apple Mail : I config a manual account that has iCloud as IMAP server for reception and Gmail as SMTP server for sending. That allows me to have sort of a double sync at the same time to iCloud and Gmail.

It was working perfectly until then, but after Sierra upgrade it keeps loosing my SMTP server config.

Following some instructions about problems with Mail and Sierra (in this thread : Re: IMAP email accounts gone in Mail after Sierra upgrade), I built up again my Mail, created new account, but the problem remains.

What happens is that it keeps losing my SMTP server. I re-entered it 20 times or more, saving it, but it mysteriously disappears. I go in Mail > Preferences > Accounts, select my manual account and this is what I see under "server settings" :

Password is gone. Username loses the "@gmail.com" part of the email address and Authentication is set to none.

If I fill up all the fiels correctly, change tab, come back : everything is gone !

I tried to delete the smtp server and create a new one, but the same happens.

Anybody is facing a similar problem ? Do you have any idea how to solve it ?

Thanks a lot for helping,

Gabriel

MacBook Pro with Retina display, macOS Sierra (10.12), null

Posted on Sep 22, 2016 5:31 PM

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Answer 1

Sep 26, 2016 12:31 AM in response to gabrielito

I have a special setup in Apple Mail : I config a manual account that has iCloud as IMAP server for reception and Gmail as SMTP server for sending. That allows me to have sort of a double sync at the same time to iCloud and Gmail.

Setup with the SMTP servers for each account. THEN in Mail > Preferences > Composing select Always send from the Gmail account.

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Answer 2

gabrielito Author

Level 1

7 points

Sep 26, 2016 12:45 AM in response to dianeoforegon

Thanks a lot Diane for your help !

Your advice helped me, not really the way that you mention, but anyway it was good.

I added in my accounts a Gmail account (automatically configured). Then, in Mail > Preferences > Account > my manual account > server settings, I could choose Google as SMTP server. This one is working.

As I don't like to have several accounts activated on my machine, I could even then de-activate the Gmail account and the Google SMTP server remains available. Looks good.

If I go as you mentioned in Mail > Preferences > Composing, I can select to send always from a certain email address, but I don't see no setting here to send through a certain SMTP server. It doesn't really serve me, as I have many email addresses all linked to the same manual account. I don't want to send always with the same address and Google allows me to use different addresses all with the same account.

So : I have solved my problem as I can send emails again. But the bug is not completely gone as manual SMTP servers seem to behave in a strange manner (disappearing).

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Answer 3

Sep 26, 2016 11:07 AM in response to gabrielito

Gmail is not regular IMAP and can result in strange behavior when used in an email app. You might be better off using your web browser to send/receive your email.

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Answer 4

gabrielito Author

Level 1

7 points

Sep 27, 2016 6:34 AM in response to dianeoforegon

Thanks again Diane for those precious informations. I didn't know that Gmail was no regular IMAP (but I could have imagined...).

As I feel efficient with Apple Mail (when it works), I prefer not using webmail if possible.

So I will stay like this now. It's unstable. Mail crashes quite often. Often, my Gmail server gets disconnected, so I use the manual one that loses the config very often. Not so good, but working. I still have an iPad beside to use Mail if needed...

I hope that a next update will solve those weird problems...

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Answer 5

Csound1

Level 9

60,063 points

Sep 27, 2016 6:40 AM in response to gabrielito

I also suggest disabling Automatic checking and maintenance of Account Settings in the advanced section of Mails account preferences.

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Answer 6

Sep 27, 2016 10:37 AM in response to gabrielito

Gmail have never been standard IMAP. Users have always had to use workarounds to get our mail to show correctly. Apple has gone a step forward in trying to get around the non-standard features.

A label in Gmail is a folder in an email app.

A message in your browser can have multiple labels and it's one message, but in an email app, each label creates a separate message.

All messages regardless of the folder are also in the All Mail folder. Mail tries to handle this so we don't see the duplicates, but you can see this is complicated.

When you send a message, Gmail's server automatically saves a copy of this message on the server. If you selected to also save the messages in account preferences you could end up with duplicates.

Hope this helps!

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Answer 7

gabrielito Author

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7 points

Sep 27, 2016 11:59 PM in response to dianeoforegon

Thanks a lot Diane. That's right, labels instead of folders might be complicated to handle...

Hopefully I save my emails only in iCloud folders and use Gmail only to send mails from different addresses.

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Answer 8

Csound1

Level 9

60,063 points

Sep 28, 2016 4:53 AM in response to gabrielito

Your mail is not in iCloud folders, it is in Gmail folders. Assuming that you send or receive using Gmail.

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Answer 9

gabrielito Author

Level 1

7 points

Sep 28, 2016 5:10 AM in response to Csound1

Thank you Csound1 for your help !

What I explained in my initial message, as I have an original setup with iCloud as incoming server and Gmail as outgoing server, I have a sort of double synchro to iCloud and Gmail at the same time...

My folders are effectively on iCloud, as I can see if I compare my iCloud webmail in Safari and Apple Mail :

Maybe it's not so surprising to have problems as this setup is not very standard... But iCloud servers only allow you to send emails with @icloud.com or @mac.com or @me.com addresses. These are my private emails, but I want to send my professional mails too without configuring a server for each of them. So my solution is the only solution I found to match my needs...

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Answer 10

Csound1

Level 9

60,063 points

Sep 28, 2016 5:12 AM in response to gabrielito

OK, now I understand, (but not approve 🙂) how come you don't want to protect your professional email as you do your personal?

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Answer 11

gabrielito Author

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7 points

Sep 28, 2016 5:16 AM in response to Csound1

I'm not sure to understand what you mean with "protect my professional email as I do my personal". Do you mean protect from Google ?

How do you manage multiple email addresses : do you configure an account for each of them ? Isn't that time consuming if you have many ? And if you change often your devices ?

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Answer 12

Csound1

Level 9

60,063 points

Sep 28, 2016 5:21 AM in response to gabrielito

Google reserves the right to disseminate information obtained from mail it sends or receives, so your Professional emails are not entirely private, nor are the replies sent to them. If you are in the EU you have laws that may help, in the US you're on your own.

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Answer 13

gabrielito Author

Level 1

7 points

Sep 28, 2016 5:25 AM in response to Csound1

Ok, I'm quite aware of the way Google uses our datas and I don't like it either.

I think I can live with that and choose to use Gmail for two reasons :

I have no critical datas that would really need to be protected from them
It permits me to receive many addresses at the same place, which is very useful

Maybe I'll change my mind if I find a better solution.

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Answer 14

Csound1

Level 9

60,063 points

Sep 28, 2016 5:34 AM in response to gabrielito

OK, as long as you know I shan't object. 🙂

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Answer 15

Nov 3, 2016 5:32 AM in response to gabrielito

I am seeing these same bugs now using Mac OS Sierra 10.12.1 with my Yahoo mail smtp server. My mail account was working flawlessly using imap to sync the folder and sending via smtp (or so I assume since it gets auto setup under internet accounts).

Anyway the bug is when I send a mail it goes into some weird sending loop forever flashing the messages once per second or so. So bug nr 1, infinite sending loop. Running the connection doctor tells me there is an auth issue with yahoo smtp server. Ok fine lets check the settings and hit bug nr 2; you cannot view the smtp settings for the mysterious now 'yahoo! offline' account (only name and description)??

Ok so maybe I'll add a new one since we get have an option that says edit smtp list. Painstakingly I get all the fields filled in and press ok expecting it to be added, but nope bug nr 3, it disappears into thin air and the account is set to 'None' over and over again.

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