MacInTouch Amazon link...

Apple Mail and email alternatives

Channels
Apple, Troubleshooting, Products
I have a MacBook Pro 2014 running High Sierra that is unable to remove no longer valid outgoing SMTP servers.

In Preferences-->Accounts-->Server Settings-->Outgoing mail Server (SMTP)-->Account, all outgoing SMTP servers are listed. Clicking the '-' in the lower left of the Edit SMTP Server List will remove the desired servers from this list, but that will not stick. The next time Mail is opened, the deleted servers reappear.

Any suggestions?

TIA
 


I have a MacBook Pro 2014 running High Sierra that is unable to remove no longer valid outgoing SMTP servers.

In Preferences-->Accounts-->Server Settings-->Outgoing mail Server (SMTP)-->Account, all outgoing SMTP servers are listed. Clicking the '-' in the lower left of the Edit SMTP Server List will remove the desired servers from this list, but that will not stick. The next time Mail is opened, the deleted servers reappear.

Any suggestions?

TIA
Do you have "Automatically detect and maintain account settings" checked in the Advanced tab of the Accounts preferences in Mail? Maybe the issue is with how your email provider has set up the account on their end. I typically leave this unchecked based on some past discussion here on MacInTouch.
 


Do you have "Automatically detect and maintain account settings" checked
No - I don't ever use that setting.

The unwanted SMTP servers are related to accounts that were once live, but have been deleted from Mail. Somehow the outgoing SMTP servers didn't get deleted at the same time.
 


Do you have "Automatically detect and maintain account settings" checked in the Advanced tab of the Accounts preferences in Mail? Maybe the issue is with how your email provider has set up the account on their end. I typically leave this unchecked based on some past discussion here on MacInTouch.
Where would I find this Advanced tab? I don't see it.
 


Here is one I encountered that has me "spitting fire". Let me first note that I didn't want to take this on... but the user was a dear friend/client when I was doing consulting. I also recommended he get it done at Apple (he was buying a new iMac). Turns out, the Apple Store charges you for this, and he went to BestBuy, as they had models $500 off. Cést la vie!

So I assisted to migrate his OS X 10.9 iMac to a macOS 10.13 new iMac (2017), because the older iMac was freezing and showing signs of artifacts (lines). He got it as a refurb, so I had no idea of past hours on it, or longevity of the hard drive.

I used an ethernet cable to transfer-migrate as I didn't have a Thunderbolt 3->2 adaptor on me (I did have the 2m cable). Do not use a hub or Airport Extreme... it caused a speed of 11MB/sec... and calculated "about 32 hours" to migrate over 500GB.

I found this out and had to cancel the migration, which cost me another hour, as I had to wipe the new iMac and restore macOS, because Migration Assistant still saw the canceled user and would not let me override/replace it!

So, ethernet-ethernet cable and 2-3 hours to migrate the iMac.

Everything came over (except Growl... not supported), but not everything worked. SIPS is not user friendly and was responsible for many issues. Quark 10 not compatible - launched, asked to activate, did, then on quit, error popup. Has to get Quark 2017. Adobe products... CS6 wanted java update but then on launch, error. Again, SIPS. We decided to get Affinity Photo to replace the old CS6 Photoshop... $49 vs $120yr.). Office 2011 works fine but complains in yellow banner: no more updates.

But the biggest frustration has to be Apple Mail. User has AOL, Verizon, iCloud and his own web email accts. AOL works. But Verizon does not. I can't get a straight answer if user knew about Verizon moving users to AOL if agreed. I was able to get his Verizon.net login to AOL.com webmail, and verified password change worked. But the settings for Mail are to use either pop.aol.com and smtp.verizon.net, or IMAP settings of imap.aol.com and smtp.aol.com. Sometimes the emails come through. Most times, Verizon email says incorrect username and password.

I dread that I am going to have to waste an entire Saturday (pro bono) removing his Verizon account from Apple Mail and losing 1000's of emails (I will back up... yes, yes) but find that either Migration Assistant did this, or some preference is corrupt on the accounts. And when you enter the username/password info, Mac Mail will sit there and not allow you to cancel or quit... for what seems like minutes. If it's wrong, it's usually immediate.

Anyone else have this issue? If I can see his emails on the web account (using his verizon.net account at AOL.com), then shouldn't IMAP be the way to go?
 



The link you provided is correct. I typed it wrong in the post, but it's correct in the Mac Mail settings for the account (incoming is imap.aol.com and outgoing is smtp.verizon.net).
But he had POP settings prior, and I tried to keep that until we were sure his emails are archived (pop.verizon.net and smtp.verizon.net). Thanks for pointing out the typo! :)
 


Let me first note that I didn't want to take this on... but the user was a dear friend/client when I was doing consulting
Just an update to this: So I had success with the user's email on the iMac, but only after disabling the previous "Verizon" account, then re-adding a new one with "same" settings. I had no success with updating.

Apple's Migration Assistant either damaged the account in migrating, or it was a corrupt preference prior to migration that prevented the account info update in Mac Mail. Or it's a flaw (feature!). I do not like how Apple doesn't not allow a manual override of email account setup. If you chose Other, you still have this "limbo" of Mac Mail checking the email address and some stored database of POP/IMAP/SMTP server settings of the "domain" you have entered. With regards to "verizon.net" account being the domain name in the email, it is not the IMAP server that it needs to be.

Even choosing AOL.Com as Aol suggests on their updated page, Mac Mail just sits there after entering the info (outgoing server is smtp.verizon.net, not smtp.aol.com). Several minutes later, you will get an error (or not, which is what I was seeing).

Now, the user has an older Verizon account disabled on Mac Mail that was POP3, and emails disappear from his account folders (I am sure they are still in his Mail directory), but he can't have both the old and new enabled. But, at least now, all devices and all accounts work. (User is 80 years old, and I give him much credit for how he still enjoys his Mac, although he agrees about the confusion - how Apple is so vague with settings and restricting our access/control to features we used to have).
 


... I do not like how Apple doesn't not allow a manual override of email account setup. If you chose Other, you still have this "limbo" of Mac Mail checking the email address and some stored database of POP/IMAP/SMTP server settings of the "domain" you have entered. ...
Rule #1: Always add accounts from inside Mail.app using its Preferences menu and then clicking Accounts. Never enter mail accounts inside System Preferences.

To ensure I can change all settings I deliberately enter a bogus email address. In Mail's Preferences click Accounts and then click +. For the address use something with random characters in the domain, e.g. foo at aowqndjds8dxngvk dot org. Since Mail can't find that domain it will show the sheet where you can enter all the info. Once the account is saved immediately click the Server Settings tab. Uncheck both checkboxes: Automatically manage connection settings.

FWIW: I just tried this in Sierra's Mail. I don't use High Sierra on a daily basis so my details could be wrong.
 


I was having an issue where I was getting automatically cc'd on emails sent to my alias for one of my Exchange accounts. The solution is to add that alias in Mail Preferences -> Accounts -> Alias drop down menu. However, for Exchange accounts set up automatically by Mac Mail, this menu is greyed out.

I found this "trick" on the Apple forums (essentially select another outgoing mail server, save that setting, then add the alias, then switch back to the correct Exchange mail server).

Sheesh. Always a chore with Mac Mail and its automagic setup of accounts.
 


(User is 80 years old, and I give him much credit for how he still enjoys his Mac, although he agrees about the confusion - how Apple is so vague with settings and restricting our access/control to features we used to have).
I work with many fellow residents here who are 80 +/-! (I'm still a young not-yet-73!) When Verizon turned their former GTE landlines over to Frontier locally and email passed to AOL, many difficulties arose. I finally was able to access a friend's Verizon.net account on AOL.com to forward all emails to her replacement Gmail account, but I don't seem to have succeeded in setting an automatic reply. AOL wanted my fellow resident to add her phone number to secure the account, but AOL both demands she choose a national code (+1) and then inserts a "+1" in front of the 10-digit local phone number she inserts, then claims the information is false!

Apparently, email has become a secondary product for these companies.

I also increasingly see Yahoo accounts being hacked to forward weight-loss ads to any and everyone. (I haven't seen any penile enhancement ads recently — perhaps in the next wave?) The website seems to indicate that Yahoo is also part of the new Oath group which has taken over AOL, but Oath does not seem to think AOL is worth mention in their brand display linked from the AOL site. An omen?
 


I would add that the new Oath user agreement I recently received would give them permission to peruse my AOL email so they can use the info for delivering targeted ads. This should be illegal, much as it is illegal to open and read someone's USPS mail without a court order. And it should be illegal to make waiving one's right a condition for delivering any product or service.
 


I would add that the new Oath user agreement I recently received would give them permission to peruse my AOL email so they can use the info for delivering targeted ads. This should be illegal, much as it is illegal to open and read someone's USPS mail without a court order. And it should be illegal to make waiving one's right a condition for delivering any product or service.
Good to know. I will pass the word.
 


Does anyone know of a way to create a POP account on iOS 11.4? My iPhone somehow got switched to IMAP, and now it does not play well with my other devices that are still POP. I did find a not-obvious way to create a POP account in High Sierra, but not iOS.

Thanks.
 


Does anyone know of a way to create a POP account on iOS 11.4? My iPhone somehow got switched to IMAP, and now it does not play well with my other devices that are still POP. I did find a not-obvious way to create a POP account in High Sierra, but not iOS.
Isn't that a server-side feature? Is the account you are adding to the phone set up as POP or IMAP?
 


Isn't that a server-side feature? Is the account you are adding to the phone set up as POP or IMAP?
Comcast offers a choice (all the ISP's I've used did). Apple seems to have taken the choice away a few revisions ago. But if you already had a POP setup, it will persist in both macOS and iOS (except for my iPhone... :-(
 


Comcast offers a choice (all the ISP's I've used did). Apple seems to have taken the choice away a few revisions ago. But if you already had a POP setup, it will persist in both macOS and iOS (except for my iPhone... :-(
That's so strange. If you go to Settings > Accounts & Passwords > Add account > other > Add Mail Account and fill in the details, doesn't it then give you POP, based on what it discovers?
 


Running El Cap on an early 2015 MacBook Air, it starts with Apple Mail not displaying the email content after selecting (single click) the message. The header is there, but no content is displayed. Now it has progressed to not displaying the content in the new window
that is presented when double clicking on the message in the left sidebar. It can be fixed temporarily by quitting and re-launching email. That was working, usually for an hour or two, now it's every couple of minutes or less. Connection Doctor shows all is well with connection to the servers.
 


While we're on Mail in iOS, I wonder if anyone can answer this:

Client has current iMac, current iPad and current iPhone. Mail settings in each are identical - I cannot see any differences.

But, the iPad only keeps mail for about 10 days unless he archives it. He swears he is not deleting it. Both the iMac and the iPhone have mails in the inbox going back since he aquired them.

Is there a secret 'thingy' in Mail that I haven't spotted?
 


Does anyone know of a way to create a POP account on iOS 11.4? My iPhone somehow got switched to IMAP, and now it does not play well with my other devices that are still POP. I did find a not-obvious way to create a POP account in High Sierra, but not iOS. Thanks.
Here is a somewhat cumbersome work-around to this: Put in an invalid email address when setting up the email account; the phone will then try to autodiscover the account settings, and when it can't, it will ask you to fill in the server details, and you can then select POP or IMAP.
 


... But, the iPad only keeps mail for about 10 days unless he archives it. ...
I'm not sure I'm answering the correct question, but this works on my iPhone:

Open Settings, then Accounts & Passwords, then tap the account, then tap Account, then at the bottom tap Advanced. Part way down you'll see Delete Messages and a Remove setting. Change it to Never. As you tap back out, be sure to tap Done instead of Cancel to save the change.
 


While we're on Mail in iOS, I wonder if anyone can answer this: Client has current iMac, current iPad and current iPhone. Mail settings in each are identical - I cannot see any differences. But, the iPad only keeps mail for about 10 days unless he archives it. He swears he is not deleting it. Both the iMac and the iPhone have mails in the inbox going back since he aquired them.
Is there a secret 'thingy' in Mail that I haven't spotted?
In the settings for the mail account, tap on "Advanced", and in that window, look at the section "Deleted Messages", and below it, "Remove". To the right is the interval, which can be changed by tapping on "Remove" and selecting one of the other three options. (There are four options: Never, After one day, After one week, and After one month.)
 


Here is a somewhat cumbersome work-around to this: Put in an invalid email address when setting up the email account; the phone will then try to autodiscover the account settings, and when it can't, it will ask you to fill in the server details, and you can then select POP or IMAP.
Thanks! That is similar to the way you can get to it in macOS, but I just couldn't find the "right" wrong thing to do to trigger that dialog... ;-)
 


In the settings for the mail account, tap on "Advanced", and in that window, look at the section "Deleted Messages", and below it, "Remove". To the right is the interval, which can be changed by tapping on "Remove" and selecting one of the other three options. (There are four options: Never, After one day, After one week, and After one month.)
Thanks to Sam and LilLC.
As I said, the settings on all three devices are the same. Only the iPad loses messages - from the Inbox, not from deleted mail - we're not bothered if it loses those.
 


Here is a somewhat cumbersome work-around to this: Put in an invalid email address when setting up the email account; the phone will then try to autodiscover the account settings, and when it can't, it will ask you to fill in the server details, and you can then select POP or IMAP.
That works in macOS too. In fact, just about any wrong or nonsense answer will bring up the more flexible dialog.
 


That's so strange. If you go to Settings > Accounts & Passwords > Add account > other > Add Mail Account and fill in the details, doesn't it then give you POP, based on what it discovers?
No, and hasn't for couple of revs of both OS's. You probably didn't notice because you already had Mail set up when you updated?
 


A new problem with Mail is driving my wife crazy. It began with the installation of macOS 10.13.5 and persists in 10.13.6. Mail does not show an e-mail as having been read after it has been opened, and will only do so if individually selected and then marked as read by the menu command. Messages can be deleted, but it turns out to be only temporary - they pop up again, and show as unread.

This happens also on her new sixth generation iPad, so I'm guessing the problem is some form of corruption in her mailboxes on iCloud, rather than in both her devices. I have tried rebuilding the Inbox on her Mac, and the issue continues. She has three e-mail accounts, one iCloud, one POP from our own domain and Gmail, which is also set up as POP. Both the latter addresses are set to forward mail to iCloud. Any ideas?
 


Is it possible what is reappearing is the original message from the POP accounts showing up after she has removed the iCloud copy? (Or, the other way around.)
 


Is it possible what is reappearing is the original message from the POP accounts showing up after she has removed the iCloud copy? (Or, the other way around.)
I wondered about that, but the POP accounts are set to delete their copy after forwarding, plus this happens whichever address the mail was originally sent to, including the iCloud address.
 


Mail does not show an e-mail as having been read after it has been opened, and will only do so if individually selected and then marked as read by the menu command. Messages can be deleted, but it turns out to be only temporary - they pop up again, and show as unread.
I am seeing this as well in the same manner. Quitting and restarting the app usually fixes the deletion problem but not the "message was read" problem.
 


A new problem with Mail is driving my wife crazy. It began with the installation of macOS 10.13.5 and persists in 10.13.6. Mail does not show an e-mail as having been read after it has been opened, and will only do so if individually selected and then marked as read by the menu command. Messages can be deleted, but it turns out to be only temporary - they pop up again, and show as unread. This happens also on her new sixth generation iPad, so I'm guessing the problem is some form of corruption in her mailboxes on iCloud, rather than in both her devices. I have tried rebuilding the Inbox on her Mac, and the issue continues. She has three e-mail accounts, one iCloud, one POP from our own domain and Gmail, which is also set up as POP. Both the latter addresses are set to forward mail to iCloud. Any ideas?
Is it the Mac that is causing the issue? Quit Mail and don’t start using it again until you can answer that question.

For a while she should use iCloud web mail and her iOS devices only and see if the problem recurs. If it does, it’s not macOS but something else. If it doesn’t, then turn off iCloud mail in iOS and only access mail through a browser.
 


A new problem with Mail is driving my wife crazy. It began with the installation of macOS 10.13.5 and persists in 10.13.6. Mail does not show an e-mail as having been read after it has been opened, and will only do so if individually selected and then marked as read by the menu command. Messages can be deleted, but it turns out to be only temporary - they pop up again, and show as unread. This happens also on her new sixth generation iPad, so I'm guessing the problem is some form of corruption in her mailboxes on iCloud, rather than in both her devices. I have tried rebuilding the Inbox on her Mac, and the issue continues. She has three e-mail accounts, one iCloud, one POP from our own domain and Gmail, which is also set up as POP. Both the latter addresses are set to forward mail to iCloud. Any ideas?
I second the other suggestions. You need to isolate which device is causing the problem. And the iCloud.com website should show you the true situation.

You said you tried rebuilding the Inbox. I'd try that again. In fact, I'd rebuild the Trash, also. Whenever Mail has weird behavior that defies explanation, you can bet that rebuilding will fix it.* And sometimes you have to rebuild more than once before it works.

Another thing to check is the Mailbox Behaviors tab in the account settings. Check that each special folder (Drafts, Sent, Junk, and especially in this case Trash) is mapped to the desired folder on either the iCloud server or a folder on your local machine. For example, what do you suppose would happen if the Trash Mailbox was actually using the iCloud Inbox?

I'm reasonably sure that the Read flag gets synced back to the IMAP server. That is, if you mark a message as read on one device, it should change it to Read everywhere. That may give you a clue to your situation. Is Mail really marking the message as read or not? What do you see on other devices or on iCloud.com? What if you read a message on another device, does it show as read on the Mac?

*Twice now I've struggled with getting Mail to properly update the Flagged message count after a migration to a new computer. In both cases the fix was to rebuild all of the mailboxes that contained flagged messages. Before doing that, the behavior was bizarre: if I un-flagged and then re-flagged a message it would correct the count, but then the next day it would be wrong again. Rinse and repeat.

Anyway, more ideas:

Are you using the classic Mail layout (Preferences Viewing tab) or the new layout? Do you have View > Organize by Conversation enabled? If so, what do you have for Preferences > Viewing > Mark all messages as read when opening a conversation?

I think that when you have messages grouped by conversation, it isn't always clear to Mail which individual messages in the conversation you've seen -- it can't tell what you're actually looking at. I have that problem on my iPhone; sometimes I just give up on getting it to mark every message in the conversation as read, because I know that when I get to my Mac (where I don't group by conversation), I can be very clear about what I've read.

Lastly, there's a strange menu item, View > Show Deleted Messages, which for me is disabled and greyed out. What do you have? I think that this would be used if the Trash mailbox was mapped to "None", so that when you delete a message it just marks it as logically deleted in the same mailbox, rather than moving it to a different mailbox.
 


I'll try some of these suggestions, but she's away again today and tonight, then home for one night and then away again for three weeks. I have to grab a chance when I can to do the maintenance!
 


I am seeing this as well in the same manner. Quitting and restarting the app usually fixes the deletion problem but not the "message was read" problem.
Ditto. Also numerous infuriating formatting issues when I make any change to a forwarded webpage article. I often use the Command+i keyboard shortcut to forward a news article to friends, and if, for instance, I highlight a phrase or sentence by changing its colour to, say, red, the entire rest of the article will go blue! WTF. I then have to Select All, make everything black again, and then repeat the highlighting. Sometimes I insert a comment or delete an advertisement, and the entire paragraph above the deleted ad will jump up ten font sizes, and/or change font. WTF again. Or I may make an overly large headline smaller and some other seemingly unrelated font will change size or type. Very annoying.

Only vaguely related to Mail, all the Groups in my Contacts, about 30 or them, duplicated themselves a few days ago, probably courtesy of iCloud. I've deleted a few of the duplicates with only a few names in them and will watch to see whether the remaining Group also disappears after a day or two before ploughing through all the other duplicate Groups and deleting one of each. With the way Apple is effing up every aspect of their system for the last few years, I'm afraid that if I just go ahead and delete all the duplicate groups I will discover that iCloud then deletes all of the remaining ones as they are somehow linked. I have no idea why they duplicated in the first place. Only the groups, not the contacts themselves, duplicated this time, unlike a few years ago when all 2000 of my contacts duplicated. Grrrr...
 


Our techs at work decided that now would be a good time to update our Exchange server to the latest release, and that seems to have broken the Mail application on Sierra. I keep getting the message "Unable to verify account name or password".

I've tried everything up to and including deleting the account and attempting to re-create it and nothing has worked.

Googling seems to indicate that this is a common occurrence, but none of the solutions I've found have worked for me. I've installed Airmail 3 and had no problem getting it to connect, but the interface to the application is putting me off, that and it doesn't seem to want to load all the messages in my inbox.

I did find a discussion on the web that Mail may not be playing nice with HTTP 2.0 and that configuring Exchange to use HTTP 1.1 seems to have solved it for those who have tried it. The only other solution was to upgrade the OS to High Sierra, but I'm waiting for it to come out of beta before taking that step.

Anyone know if there's some terminal voodoo or hidden settings that I can use to resolve the issue?
 



I second the other suggestions. You need to isolate which device is causing the problem. And the iCloud.com website should show you the true situation. ...
Another possibly useful troubleshooting approach might be to use a different IMAP client on your Mac to connect to the iCloud mailbox. Mozilla Thunderbird might be a good alternative. If the problem is seen there as well, then it is probably an iCloud (or less likely, a network) problem. If the problem does not occur with Thunderbird, then it is almost definitely a Mail.app problem.
 




*Twice now I've struggled with getting Mail to properly update the Flagged message count after a migration to a new computer. In both cases the fix was to rebuild all of the mailboxes that contained flagged messages. Before doing that, the behavior was bizarre: if I un-flagged and then re-flagged a message it would correct the count, but then the next day it would be wrong again. Rinse and repeat.
I was having this very same problem and was escalated to Engineering at AppleCare to solve it. It turned out to be a Spotlight problem. Flags are detected by Spotlight. Engineering recommended that I run the following Terminal command:
Bash:
sudo find /var/folders/zz -name "*.csstore" -delete; sudo reboot
and the flags immediately began behaving properly again.
 


Amazon disclaimer:
As an Amazon Associate I earn from qualifying purchases.

Latest posts