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Yesterday when sending from my .Mac account Apple mail burped saying that my sender address was rejected by the server p38-smtp.mail.me.com, suggesting in the drop down sheet that I should choose [my email address]@mac.com, which is where I was sending to anyway. I clicked on Try with Selected Server, which highlighted [my email address]@mac.com, and the outgoing mail then departed as it should have done originally. I have had this happen twice this week, but since, it has not happened again - so far!
 



Yesterday when sending from my .Mac account Apple mail burped saying that my sender address was rejected by the server p38-smtp.mail.me.com, suggesting in the drop down sheet that I should choose [my email address]@mac.com, which is where I was sending to anyway. I clicked on Try with Selected Server, which highlighted [my email address]@mac.com, and the outgoing mail then departed as it should have done originally. I have had this happen twice this week, but since, it has not happened again - so far!
I had something similar happen when trying to send a message using my Verizon.net (now actually AOL) account last week in Mail.app under macOS 10.14. It only happened once, despite several messages sent using that account on that day. The diagnostics were less extensive, however (just "couldn't send" using that server, if I recall correctly).
 


Yesterday when sending from my .Mac account Apple mail burped saying that my sender address was rejected by the server p38-smtp.mail.me.com, suggesting in the drop down sheet that I should choose [my email address]@mac.com, which is where I was sending to anyway. I clicked on Try with Selected Server, which highlighted [my email address]@mac.com, and the outgoing mail then departed as it should have done originally. I have had this happen twice this week, but since, it has not happened again - so far!
I've been having this same issue for the last couple of days. Apple Mail refused to send anything via iCloud using my ******@mac.com on the first try. Subsequent tries usually succeeded without making any changes. In each case, the error message on the drop-down sheet said Apple didn't recognize my email address - the same email address I've had since iTools' first day.

But the issue seems to be getting worse over time. I tried several times earlier today, and it absolutely wouldn't send even on the second or third attempt. Finally I changed my "send from" to ******@icloud.com, and it took it. But then another email right after, using the @icloud.com address, wouldn't go, with the drop-down sheet complaining.

Yet I'd cc'd myself on that email, and it came though just fine. So I'd say something is very wrong at Apple itself and has nothing to do with Apple Mail, my accounts or preferences. Apple says it's just fine and dandy, but it obviously isn't.
 


So I'd say something is very wrong at Apple itself and has nothing to do with Apple Mail, my accounts or preferences. Apple says it's just fine and dandy, but it obviously isn't.
As a second test, I booted my MacBook Pro for the first time in two weeks, just to see if perhaps some Apple Mail preference had gotten corrupted somehow. This issue started just last Saturday, and the MacBook Pro's Apple Mail functioned perfectly when it was last used two weeks prior. Sure enough, I immediately got the same drop-down sheet with the same complaint when I tried to send an email through iCloud.

So it appears to not be a corrupted preference or account. It helps that it's not happening just to me, that at least some others are affected by this same error. We can't all have done the same "user error" at the same time.
 




I've been having this same issue for the last couple of days. Apple Mail refused to send anything via iCloud using my ******@mac.com on the first try. Subsequent tries usually succeeded without making any changes. In each case, the error message on the drop-down sheet said Apple didn't recognize my email address - the same email address I've had since iTools' first day.

But the issue seems to be getting worse over time. I tried several times earlier today, and it absolutely wouldn't send even on the second or third attempt. Finally I changed my "send from" to ******@icloud.com, and it took it. But then another email right after, using the @icloud.com address, wouldn't go, with the drop-down sheet complaining.

Yet I'd cc'd myself on that email, and it came though just fine. So I'd say something is very wrong at Apple itself and has nothing to do with Apple Mail, my accounts or preferences. Apple says it's just fine and dandy, but it obviously isn't.
Same thing is happening to me (Mojave/MacBook Air). Trying to send emails from my iCloud account results in a hung send. Only sometimes will Mail.app offer me the window to pick a different outgoing server. Mostly I just get a partial blue line in the "Sending" status. Sending mail from my iPhone also doesn't work. iCloud Mail system status is green.

However, trying to send a test email direct from iCloud.com results in: "This message cannot be sent at this time. Try again later."
 


So it appears to not be a corrupted preference or account. It helps that it's not happening just to me, that at least some others are affected by this same error. We can't all have done the same "user error" at the same time.
About a week ago, I started having problems with my Apple Mail email as well. I'm posting my situation to see if it will help solve yours.

macOS Sierra on a desktop and laptop, using Apple Mail as a POP account (with desktop as the master), no IMAP except on the phone, no iCloud interference.

iOS Mail on my phone with the latest iOS had no problems with the accounts. ISP is ATT/Yahoo, and my main email address is through them. Gmail POP addresses not affected.

Everything had worked fine since the Sierra upgrade a few years ago. Suddenly, neither my desktop nor laptop would send or retrieve mail... at the same time. I got the same drop-down menu to choose another server. ATT tech support guy (with his brain in IMAP-land) advised me to delete the email address in Apple Mail and add them again. That is what I eventually did, after dragging my current Inbox and Sent items to new mail folders in On My Mac, so I wouldn't lose the mail. I then recreated the email addresses on the Macs, and everything worked again.

Because it happened on both Macs at the same time, it was something ATT Yahoo did, not some software corruption. I know they recently instituted new security encryption, and I'm wondering if maybe my legacy email accounts were somehow originally set up in a way that the servers now rejected. Sierra's version of Apple Mail was supposed to be able to handle the new encryption, but maybe an earlier OS hadn't let the servers know whatever little bit of info was now needed when the accounts were first verified by the servers years ago. Anyway, deleting and adding the email accounts again fixed my problem.
 



I'm having the same problem with my mac.com email address from January 5, 2000. Likewise, my wife is having the same problem with hers, as well. Sigh. (As if the two-factor authentication and app-specific password fiasco wasn't bad enough...)
 


Yesterday when sending from my .Mac account Apple mail burped saying that my sender address was rejected by the server p38-smtp.mail.me.com, suggesting in the drop down sheet that I should choose [my email address]@mac.com, which is where I was sending to anyway. I clicked on Try with Selected Server, which highlighted [my email address]@mac.com, and the outgoing mail then departed as it should have done originally. I have had this happen twice this week, but since, it has not happened again - so far!
I started having this problem today but with a different server, pxx-smtp.mail.me.com. I can receive mail sent to my Apple accounts. I can send e-mail when I log onto iCloud on the web, although as some of you know, to do this on my iPad, I had to use Safari and request a desktop account.

For a couple of days last week, Apple was real slow sending mail and wasn't saving messages to Sent Mail on my device’s mail account. I copied myself so I'd have a copy of the message. That resolved itself after a couple of days.

I went to Apple support forums and saw that others were having the same trouble. Someone had a chat with Apple, who said they were having trouble with one of their mail servers.
 


Yesterday when sending from my .Mac account Apple mail burped saying that my sender address was rejected by the server p38-smtp.mail.me.com, suggesting in the drop down sheet that I should choose [my email address]@mac.com, which is where I was sending to anyway. I clicked on Try with Selected Server, which highlighted [my email address]@mac.com, and the outgoing mail then departed as it should have done originally. I have had this happen twice this week, but since, it has not happened again - so far!
I'm having the same problem with my mac.com email address from January 5, 2000. Likewise, my wife is having the same problem with hers, as well. Sigh. (As if the two-factor authentication and app-specific password fiasco wasn't bad enough...)
i have just had the same server rejection after a day or two of no problems. A rejected message was sent from my iMac, but I noticed it had been rejected while checking my iPhone mailbox. The trouble was I could not access it to either resend or delete. I restarted the iPhone and was able to dispatch the email.
 



Ric Ford

MacInTouch
I spoke with someone at Apple Technical Support about an hour ago. They acknowledged that there definitely is a problem, Apple is aware of it, and their engineers are working on it. The problem is that the iCloud Status Page does not show that there's an issue.
The latest update shows a problem that's supposedly resolved:
Apple said:
iCloud Mail - Resolved Issue
Today, 4:30 PM - 8:37 PM
Some users were affected
Users may have been unable to send iCloud mail.
...
Last updated today, 10:07 PM Eastern Daylight Time.
 


KJM

I had the SMTP issue, too. When I looked into it, I noticed that obviously some IMAP mail accounts (not only iCloud) had lost their "Default SMTP Server" setting — and changes did not stick. I created some test mails to another account of myself, and when I tried to send those mails, a dialog popped up and allowed to choose and set a Default SMTP server for my sending account. I had to recreate missing server settings for some Yahoo accounts. Issue solved.
 


The latest update shows a problem that's supposedly resolved:
I can confirm my iCloud emails now send correctly. My issues have been resolved, at least until the next time, I suppose.

All this would've been far easier on me if Apple had just fessed up on their Apple Status web page that iCloud mail was having an issue. I checked there several times since last Saturday when the issues started, only to find Apple claiming everything was perfect. If they'd just acknowledged the issues they were having I wouldn't have had to go through all the troubleshooting steps for nothing.
 


I can confirm my iCloud emails now send correctly. My issues have been resolved, at least until the next time, I suppose. All this would've been far easier on me if Apple had just fessed up on their Apple Status web page that iCloud mail was having an issue. I checked there several times since last Saturday when the issues started, only to find Apple claiming everything was perfect. If they'd just acknowledged the issues they were having I wouldn't have had to go through all the troubleshooting steps for nothing.
It has been suggested to me that the email about the issue never arrived to the person in charge of changing the green dots to red.
 


I have earlier reported that some Mail attachments seem to be stuck when downloading. Some images will display a generic icon with a name plus "downloading…". This had affected my Mac for some time (3+ years?) but not my wife's. She recently updated to Mojave and now has the identical problem. The attachments are sent from macOS/iOS and Windows/Android users and to our own domain IMAP and iCloud accounts.

It is so frustrating, and we haven't found any way to solve it. We are semi-retired designers, who are used to having hundreds of images sent as attachments every week, from the whole gamut of sources. Recently I resorted to running my own ftp server just to provide a temporary solution, but it seems so old fashioned and a real hassle as well.
 


Ric Ford

MacInTouch
We are semi-retired designers, who are used to having hundreds of images sent as attachments every week, from the whole gamut of sources. Recently I resorted to running my own ftp server just to provide a temporary solution, but it seems so old fashioned and a real hassle as well.
Dropbox may be a fairly easy solution. (I'm also looking into other options currently.)
 


I have earlier reported that some Mail attachments seem to be stuck when downloading. Some images will display a generic icon with a name plus "downloading…". This had affected my Mac for some time (3+ years?) but not my wife's. She recently updated to Mojave and now has the identical problem. The attachments are sent from macOS/iOS and Windows/Android users and to our own domain IMAP and iCloud accounts.

It is so frustrating, and we haven't found any way to solve it. We are semi-retired designers, who are used to having hundreds of images sent as attachments every week, from the whole gamut of sources. Recently I resorted to running my own ftp server just to provide a temporary solution, but it seems so old fashioned and a real hassle as well.
In case you've missed this previously, are these messages being moved to other mailboxes/folders by rules? If so, then what's happening is the messages are being moved before the downloading can complete. I have a bug report opened on this. The best thing to do is to "turn off" the rules that move the messages to the mailbox(es). You don't have to delete the rule, just uncheck the box so it's not active.
 


In case you've missed this previously, are these messages being moved to other mailboxes/folders by rules? If so, then what's happening is the messages are being moved before the downloading can complete. I have a bug report opened on this. The best thing to do is to "turn off" the rules that move the messages to the mailbox(es). You don't have to delete the rule, just uncheck the box so it's not active.
I hadn't thought of the movement causing it. I'll turn that off and see what happens.
 


In case you've missed this previously, are these messages being moved to other mailboxes/folders by rules? If so, then what's happening is the messages are being moved before the downloading can complete. I have a bug report opened on this. ...
Jay, we can confirm that moving messages automatically to other mailboxes and folders causes the failed download attachment and message. It seems that Mail loses the link to the file as it is shoved around by Mail rules.

In the process of solving that bug, we've found that our Time Machine back-up won't let us get into our Time Machine…User/Library/ crash. Which is most annoying, as Sophos has found some infected attachments - Windows-only, thankfully.
 


Jay, we can confirm that moving messages automatically to other mailboxes and folders causes the failed download attachment and message. It seems that Mail loses the link to the file as it is shoved around by Mail rules.
In the process of solving that bug, we've found that our Time Machine back-up won't let us get into our Time Machine…User/Library/ crash. Which is most annoying, as Sophos has found some infected attachments - Windows-only, thankfully.
Glad to hear it's the same issue. I think what is happening is the rules are applied too quickly - my 2011 MacBook Pro never experienced this. I noticed it once I got this new laptop (2018 MacBook Pro) that is much faster. Hopefully, this will be fixed soon, since there are open bug reports against it.

Bummer about the Time Machine backups. Have you tried mounting it and going to it via the Finder instead of via Time Machine? If you can do that, maybe you can delete the offending/infected files.
 


Glad to hear it's the same issue. I think what is happening is the rules are applied too quickly - my 2011 MacBook Pro never experienced this. I noticed it once I got this new laptop (2018 MacBook Pro) that is much faster. Hopefully, this will be fixed soon, since there are open bug reports against it.

Bummer about the Time Machine backups. Have you tried mounting it and going to it via the Finder instead of via Time Machine? If you can do that, maybe you can delete the offending/infected files.
I wonder if there is any way to slow down Mail rules? Currently we have edited the Move rule to become Copy.

The Time Machine glitch cleared itself up by the next day.
 


I restarted my 2010 Mac Mini running High Sierra this morning, because it had slowed down badly, and when it rebooted, Apple Mail had lost track of signatures for all my email accounts. I started rebuilding them, but after a couple of minutes I clicked on "all signatures" in the signatures preference item, and the missing signatures reappeared there but had to be rebuilt for the other accounts. Any idea what's going on? Was that just extreme slowness at an odd time or what?
 


I restarted my 2010 Mac Mini running High Sierra this morning, because it had slowed down badly, and when it rebooted, Apple Mail had lost track of signatures for all my email accounts. I started rebuilding them, but after a couple of minutes I clicked on "all signatures" in the signatures preference item, and the missing signatures reappeared there but had to be rebuilt for the other accounts. Any idea what's going on? Was that just extreme slowness at an odd time or what?
A delay in contacting the iCloud mother ship?
 


I was with a client yesterday to do some general housekeeping and noticed that the Mail activity viewer showed that it was sending something. After 15 minutes it was still sending.
I commented to her, and she said, "oh, that's been there over a month now!"

There was nothing in the outbox, no activity progress bar, no drafts or anything I could see - and no network traffic.

Any thoughts would be appreciated.
 


I was with a client yesterday to do some general housekeeping and noticed that the Mail activity viewer showed that it was sending something. After 15 minutes it was still sending.
I commented to her, and she said, "oh, that's been there over a month now!"
There was nothing in the outbox, no activity progress bar, no drafts or anything I could see - and no network traffic.
Any thoughts would be appreciated.
Is there an "Out" (or something similar) mailbox visible? That only appears when an outgoing message is not sent for some reason or is taking a long time (and I think a month qualifies). If so, you could try deleting whatever is there.
 


I was with a client yesterday to do some general housekeeping and noticed that the Mail activity viewer showed that it was sending something. After 15 minutes it was still sending.
I commented to her, and she said, "oh, that's been there over a month now!"
There was nothing in the outbox, no activity progress bar, no drafts or anything I could see - and no network traffic.
Is there an "Out" (or something similar) mailbox visible? That only appears when an outgoing message is not sent for some reason or is taking a long time (and I think a month qualifies). If so, you could try deleting whatever is there.
Had a similar issue with a client who tried to email 200+ MB of photographs in one email. Kept trying to send, and we only got it to appear in the Outbox by pulling the network cable and then launching Apple Mail. Once deleted, all was well with the network cable connected again.
 


I have found that the mail 'message list' occasionally shows a sender's email address instead of their name, even though their name is in my contacts list. This happens only for a few of my contacts and, curiously, is fixed if I select the small button at the top of the message list to show only 'unread' messages and then un-select it, after reading the message. In other words, forcing the message list to re-display always then correctly displays the sender's name, as it should. I would be most grateful if someone could tell me how to fix this trivial but annoying problem.
 


When someone sends me a mail message with an attachment, I often wish to save
the message in Mail.app but without the attachment. I used to be able to select
Message => Remove Attachments to do this. In Mojave and High Sierra, that
menu choice is grayed out for me.

I could not check permissions on
~/Library/Containers/com.apple.mail/Data/Library/Mail Downloads
without booting into Recovery and disabling SIP. Each directory in "Mail Downloads" has
the "com.apple.quarantine" extended attribute - maybe this is related to my problem.

I also notice that starting in Mojave, as I read through messages in my Inbox,
deleting a message and going to the next sometimes comes up with a blank pane.
(I use the "classic layout" on POP accounts.) Viewing some other mail folder and
then switching back to the Inbox will cause the message content to appear.
 


When someone sends me a mail message with an attachment, I often wish to save the message in Mail.app but without the attachment. I used to be able to select Message => Remove Attachments to do this. In Mojave and High Sierra, that menu choice is grayed out for me.
I have the same problem with macOS Sierra Mail.app. The "Remove Attachments" option was working fine in El Capitan. The day I upgraded to Sierra, I noticed the issue on the exact same emails from earlier in the day. At that time, I did some searching and at least one poster said that this "grayed out issue" was fixed in High Sierra and Mojave, but I guess not. I'd love to find a fix for this, because I have no plans to go beyond Sierra.
 


I could not check permissions on
~/Library/Containers/com.apple.mail/Data/Library/Mail Downloads
without booting into Recovery and disabling SIP. Each directory in "Mail Downloads" has
the "com.apple.quarantine" extended attribute - maybe this is related to my problem.
Hmm. Not only is the "Remove Attachment" not grayed out on my Mojave install, but I had no problem viewing permissions and extended attributes for any of the folders in that directory. It is in my home directory, after all. The quarantine extended attribute was set on some files (attachments) but was not set for any of the containing folders.
 


have the same problem with macOS Sierra Mail.app. The "Remove Attachments" option was working fine in El Capitan. The day I upgraded to Sierra, I noticed the issue on the exact same emails from earlier in the day. At that time, I did some searching and at least one poster said that this "grayed out issue" was fixed in High Sierra and Mojave, but I guess not. I
Hmm. Not only is the "Remove Attachment" not grayed out on my Mojave install, but I had no problem viewing permissions and extended attributes for any of the folders in that directory.
I don't normally use "Remove Attachments" but am on High Sierra, and when I tested it in Mail, it worked. It then grayed out, because the attachment was gone, but "Remove Attachments" became available again once I went down to another mail with an attachment. I have a mixture of POP and IMAP accounts, and use a "classic" layout.

FWIW, I also have been seeing blank contents in some mails at times, but I have not taken the time to diagnose what's happening.
 


Ric Ford

MacInTouch
I also have been seeing blank contents in some mails at times, but I have not taken the time to diagnose what's happening.
FWIW, I've seen this happen in Apple's Mail on iOS (latest version), which seems a little flaky vs. Postbox on my macOS Sierra system, but I haven't spent any time investigating it.
 


I have been a happy Apple Mail via POP user for years. I have been using SpamSieve for a long time.

About a year ago I moved to using IMAP, so that my iPhone and MacBook Pro were aways in sync. Please could someone help me understand the "On My Mac" mail account? I see this below the list of Smart Mailboxes. It was my understanding that all mail from an IMAP account would remain on the mail server side. What is "On My Mac", and can I remove it? Thanks
 


I'm seeing a problem in macOS Sierra Mail where attachments in my POP account often do not show in the Attachments column, the Remove Attachments menu item is dimmed, but the attachment info does show up in the popup toolbar thing between the header and message body, and they do show up in the message. It's inconsistent. I am not sure when this started happening. Doesn't seem to happen on my Exchange account.
 


When someone sends me a mail message with an attachment, I often wish to save
the message in Mail.app but without the attachment. I used to be able to select
Message => Remove Attachments to do this. In Mojave and High Sierra, that
menu choice is grayed out for me.
I have had this problem even with older versions of the OS. Someone suggested long ago that this can be fixed by adding the following "Rule" in Mail Preferences:

If all of the following conditions are met
Any attachment name contains .
<==(Note: the name contains a period)
Perform the following actions:
Mark as Read


I'm not sure if this rule is doing the trick, but I can delete attachments on most messages. Occasionally, however, a message will still have an undeletable attachment. I can fix this by dragging the message to the desktop and deleting the attachment with a text editor.
 


Mom's iMac (macOS 10.13.6) has been having an unusual issue I can't seem to solve. It involves how links in Mail.app open in Safari.

If she clicks on a link in an email (usually a Pinterest mailing but others, too), Safari comes to the front, and a Yahoo search page appears (her default search engine is DuckDuckGo). If she goes back to the email and clicks the link again, the correct Pinterest page appears. This is always the case: first click -> Yahoo, second and subsequent clicks -> actual link.

If she right-clicks and chooses "open link", she never gets the Yahoo page. Change the default browser to Chrome, and the first click now goes to the correct page in Chrome. If she forwards me the Pinterest email, all the links open as they should in Safari.

I tried deleting the com.apple.mail.plist file in Preferences, but I don't think that is being used anymore, since it didn't create a new one when I re-launched Mail.app. Is the PersistenceInfo.plist file in the Preferences/Mail folder now the general preferences file for Mail? I didn't have time to test trashing that this afternoon.

So, any ideas why it's the Yahoo search page that opens? Besides trashing preferences, is there anything else I can try?
 


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