Ask Different (Apple)
Q&A for power users of Apple hardware and software
Latest Questions
4
votes
2
answers
1387
views
How to hide Gmail labels in Apple Mail?
When searching for mail in Mail.app with a Gmail account, every instance of the mail shows up with every Gmail label, especially in the Bin label, since Apple mail autosaves drafts as you go along, there can be 50 instances of a single mail just in the Bin folder. This makes searching impossible. So...
When searching for mail in Mail.app with a Gmail account, every instance of the mail shows up with every Gmail label, especially in the Bin label, since Apple mail autosaves drafts as you go along, there can be 50 instances of a single mail just in the Bin folder.
This makes searching impossible.
So I'm trying to turn off those labels in Gmail but no success so far. I have disabled "Show in IMAP" option in the Gmail label settings for all those labels then deleted all the cached items in ~/Library/Mail/V2 and restarted Mail.app but that didn't do the trick.
kLy
(2778 rep)
Mar 8, 2013, 05:19 PM
• Last activity: Aug 1, 2025, 12:09 AM
2
votes
1
answers
354
views
Apple Mail keeps marking mail as deleted when moving from junk to inbox
The following scenario occurs regularly on several of my e-mail accounts (all IMAP accounts): - I receive a valid e-mail, but it is marked as spam and shows up in my Junk folder (though not usually actually _marked_ as spam) - I click “Move to Inbox” to move it out into my inbox since it’s not spam...
The following scenario occurs regularly on several of my e-mail accounts (all IMAP accounts):
- I receive a valid e-mail, but it is marked as spam and shows up in my Junk folder (though not usually actually _marked_ as spam)
- I click “Move to Inbox” to move it out into my inbox since it’s not spam
- The e-mail shows up in my inbox, but then within a minute or two vanishes, sometimes before my very eyes, _while_ I’m actually reading it
If I log on using a webmail system which shows items marked for deletion using strikethrough, I can see the missing e-mail, so it appears that Mail, for some reason, is flagging it for deletion, but without actually moving it to the Bin folder where delete-flagged items would normally be.
Unfortunately, the webmail systems I have access to don’t seem to offer any way to add or remove IMAP delete flags, and I can’t find any way to do so in Apple Mail either.
On a few of the accounts, I have access to the MailEnable Administration, but while I can see the message (as a .mai file) in the user’s inbox there, I can’t figure out how to see or edit IMAP flags on messages, aside from editing the raw XML index file (which is risky, since it may lead to corruption if an e-mail arrives while the file is being edited). And it also happens with other accounts that I have no admin access to, anyway.
Short of nuke-style approaches like rebuilding/reinstalling entire mailboxes, is there some way to retrieve items that Mail flags for deletion without moving?
(This has been happening regularly for years, across several Macs (Intel Mac mini, M1 MacBook Pro, M1 Mac Studio) running at least macOS Catalina/10.15 to Ventura/13.3.)
Janus Bahs Jacquet
(437 rep)
Apr 15, 2022, 05:52 PM
• Last activity: Jul 29, 2025, 10:10 AM
2
votes
1
answers
1759
views
How to login to IMAP client using custom domain mail?
I recently moved from outlook to icloud-mail (as it's free) using my custom domain. Switching was easy, now I'm trying to move my existing mails from outlook to icloud mail. I've decided that I will login both my outlook and icloud-mail accounts via IMAP on thunderbird and would then simply copy eve...
I recently moved from outlook to icloud-mail (as it's free) using my custom domain. Switching was easy, now I'm trying to move my existing mails from outlook to icloud mail.
I've decided that I will login both my outlook and icloud-mail accounts via IMAP on thunderbird and would then simply copy everything from outlook->icloud.
The problem I'm facing is that I can't login on thunderbird. When I enter my custom-domain email thunderbird finds the correct imap/smtp hostnames etc., but when I try to login using an app-password (2FA is enabled) I get an error stating username/password doesn't work.
I also tried it with my
@icloud.com
mail, following this article: https://support.apple.com/en-us/HT202304
But this ended with the same result. Now is it even possible to login with IMAP to my custom domain mail?
baltermia
(139 rep)
Nov 9, 2022, 07:48 AM
• Last activity: Jul 27, 2025, 04:05 AM
4
votes
2
answers
4706
views
How fix MacOS Mail so Gmail labels appear?
I recently bought a new MacBook Pro, and set up Mac Mail with my Gmail accounts. At first, when the mail was being imported, the labels for my emails listed in the list preview section of the Inbox / message browser appeared. Then, Mac ran an update for 10.15 (Catalina), and all of the labels for my...
I recently bought a new MacBook Pro, and set up Mac Mail with my Gmail accounts. At first, when the mail was being imported, the labels for my emails listed in the list preview section of the Inbox / message browser appeared. Then, Mac ran an update for 10.15 (Catalina), and all of the labels for my emails listed in the list preview section of the Inbox / message browser ***disappeared***.
I've ensured that the 'Show in IMAP' checkbox is ticked next to all of the labels I wish to see as folders in Apple Mail. It shows the mailbox but not the labels for the messages listed in the list preview section of the Inbox / message browser.
Any ideas on how to fix this? I've contacted Apple support, but they haven't provided any guidance.
user12228535
(41 rep)
May 2, 2020, 07:03 AM
• Last activity: Jun 23, 2025, 07:03 AM
0
votes
0
answers
36
views
How to make mailbox behaviours stick?
This has annoyed me for years and years, so now I’m asking. Whenever I try to change the _Mailbox behaviours_ settings in Mail.app, the settings randomly revert to their previous value. Specifically, I **never** want to use the _On my Mac_ → _All [folder]_ option on IMAP accounts – my drafts, sent,...
This has annoyed me for years and years, so now I’m asking.
Whenever I try to change the _Mailbox behaviours_ settings in Mail.app, the settings randomly revert to their previous value.
Specifically, I **never** want to use the _On my Mac_ → _All [folder]_ option on IMAP accounts – my drafts, sent, junk and bin mailboxes should always be the corresponding folder on the server. But setting this up is an uphill battle of Sisyphean proportions.
When I change, say, the _Drafts Mailbox_ option to _[Account]_ → _Drafts_, what most commonly happens is that after a few seconds (anywhere between two and ten), the setting jumps back to _On my Mac_ → _All Drafts_.
If I change it again, it usually sticks… or rather, looks like it sticks. If I move to another account in the list on the left and then back to the account I just altered, it’s jumped back to _All Drafts_ again.
Usually, if I then only change _one_ setting and jump back and forth between accounts, it will eventually stick – sometimes after three or four attempts, sometimes after twenty or thirty attempts. Other times, it seems to just flat-out refuse to stick no matter how many times I change it.
And then, seemingly at random (or perhaps related to OS updates), it will suddenly reset **all folders on all accounts** to the _On my Mac_ → _All [stuff]_ folders, and I can start all over again trying to fix it one by one.
This has been happening on at least three different Macs (Intel Mac mini, M1 Mac Studio and M1 MacBook Pro) for at least four or five years, since whatever version of macOS I was using back then up through Sequoia 15.5 that I’m on now.
**Is there a more stable and reliable way to set Mail.app’s mailbox behaviours to make sure they stick?**
Janus Bahs Jacquet
(437 rep)
Jun 13, 2025, 11:40 AM
• Last activity: Jun 13, 2025, 02:48 PM
0
votes
2
answers
855
views
Ensure macOS mail application is downloading and keeping locally all messages with IMAP
I have an IMAP email account. I am reading my e-mails with macOS Mail application. Emails are kept on server. It seems they are also kept locally but I am not sure if it is a temporary cache. Is there a way to be sure ALL emails (and attachment) will be kept on my local computer ? Thanks
I have an IMAP email account.
I am reading my e-mails with macOS Mail application.
Emails are kept on server.
It seems they are also kept locally but I am not sure if it is a temporary cache.
Is there a way to be sure ALL emails (and attachment) will be kept on my local computer ?
Thanks
Bob5421
(151 rep)
Apr 11, 2024, 01:04 PM
• Last activity: May 6, 2025, 11:06 PM
0
votes
1
answers
993
views
Moving mail from permanently offline account's inbox (macOS Mail.app)?
I have an old, no longer accessible IMAP account (or two) with mail that I need off of it. I can access the mail in this defunct account (cached/local copies now on my machine); but my attempts to move the emails in the inbox, or even copy them, fail. Is there some other way to export them to a mail...
I have an old, no longer accessible IMAP account (or two) with mail that I need off of it. I can access the mail in this defunct account (cached/local copies now on my machine); but my attempts to move the emails in the inbox, or even copy them, fail. Is there some other way to export them to a mailbox on my hard drive (within Mail.app)?
Paul Bruno
(113 rep)
Jul 12, 2019, 07:50 PM
• Last activity: May 1, 2025, 07:03 PM
1
votes
1
answers
174
views
How can I change the port used by a Mac Mail account?
I've added a new account via Mac Mail. The host uses port 993 for IMAP, and 543 for SMTP, with the same username and account for each. I unchecked "Automatically manage connection settings" and set that up, and Mac Mail has successfully connected to the SMTP server, but not the IMAP server. I have d...
I've added a new account via Mac Mail. The host uses port 993 for IMAP, and 543 for SMTP, with the same username and account for each. I unchecked "Automatically manage connection settings" and set that up, and Mac Mail has successfully connected to the SMTP server, but not the IMAP server. I have double- and triple- checked that the settings I entered are correct. I've also tried checking "Automatically manage connection settings".
Checking the logs, in all cases, it's using port 143 for IMAP, ignoring what I've entered via the UI.

READ Apr 22 08:02:01.178 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:REDACTED -- port:143 -- socket:0x600012e11860 -- thread:0x600009fe3c00
7.614 NO [AUTHENTICATIONFAILED] Authentication failed.
WROTE Apr 22 08:02:01.179 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:REDACTED -- port:143 -- socket:0x600012e11860 -- thread:0x600009fe3c00
8.614 LOGIN USERNAME_REDACTED ********************
READ Apr 22 08:02:03.243 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:REDACTED -- port:143 -- socket:0x600012e11860 -- thread:0x600009fe3c00
8.614 NO [AUTHENTICATIONFAILED] Authentication failed.
WROTE Apr 22 08:02:03.244 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:REDACTED -- port:143 -- socket:0x600012e11860 -- thread:0x600009fe3c00
9.614 LOGOUT
I'm on Sequoia, but from the various threads on the apple support websites, it seems like the UI for this hasn't worked for coming up on a decade. It's the same if I add the account via the Internet Accounts setting in the System Settings app.
So - how can I change the port used by a Mac Mail account? Is there a plist I can edit, or some command I can run from the terminal, to set the port that Mac Mail will use? To be completely clear, I'm not looking for any answers involving the broken Mac Mail or System Settings UI.
Simon
(398 rep)
Apr 21, 2025, 08:47 AM
• Last activity: Apr 23, 2025, 06:19 AM
0
votes
0
answers
40
views
Import a HUGE Gmail mailbox in Apple Mail
One of our managers has a huge Gmail mailbox, ~400GB. They started it when it was more human-sized, managed with Apple Mail. Growing over time wasn't apparently a problem for a 2021 MBP with 32GB of RAM. Now they had to change the computer and we didn't have the chance to migrate the profile on the...
One of our managers has a huge Gmail mailbox, ~400GB.
They started it when it was more human-sized, managed with Apple Mail. Growing over time wasn't apparently a problem for a 2021 MBP with 32GB of RAM.
Now they had to change the computer and we didn't have the chance to migrate the profile on the new device, so we had to start a new sync from scratch. This proved to be a nightmare!
Gmail is enforcing an IMAP hourly (or daily) data transfer limit of ~1.5GB. This makes it impossible to feed Mail from IMAP directly.
We did a Google Takeout of the mailbox, and we now have this multi-Gigabyte Mbox file. Trying to import it in Mail hangs it, reaching ~95GB of consumed RAM (out of the 48 physically available).
So I was wondering if there's some other way to load this file directly in Mail without passing through the import. Maybe placing the file (original or converted) into Mail data dir, and letting it reindex later.
If this is not possible, is there any other way to work with this Mbox file?
thanks
Maxxer
(166 rep)
Feb 27, 2025, 04:55 PM
1
votes
1
answers
504
views
Mail server settings always gets an error
I wanted to add an iCloud address in gmail. I've entered everything correctly, hoping to show SMTP setting. But instead, it shows incorrect username and password, even also got stuck in the loading screen. I've entered the app specific password, correct imap server, correct user name based on [Mail...
I wanted to add an iCloud address in gmail. I've entered everything correctly, hoping to show SMTP setting. But instead, it shows incorrect username and password, even also got stuck in the loading screen. I've entered the app specific password, correct imap server, correct user name based on Mail server settings for iCloud email clients .


Calvin Tanuri
(58 rep)
Dec 1, 2021, 02:50 AM
• Last activity: Apr 19, 2024, 07:03 PM
6
votes
2
answers
1796
views
Recovering emails from defunct IMAP account
I have an IMAP account within Mail.app which was recently “killed” (moved to a different provider to be precise). Unfortunately, I was not able to do a backup beforehand, because I received the admin’s notification about the upcoming infrastructure change too late. Actually, I didn't suspect any big...
I have an IMAP account within Mail.app which was recently “killed” (moved to a different provider to be precise). Unfortunately, I was not able to do a backup beforehand, because I received the admin’s notification about the upcoming infrastructure change too late.
Actually, I didn't suspect any big issue moving the messages from the mailboxes from the old to the new server (after all, Mail.app seems to be caching all messages for offline reading anyways). But this assumption was probably too simple. I made the following attempts:
1. My old email mailboxes were still in Mail.app, but showing the 'warning' badge to indicate that the server was no longer working. So I simply set up the new email account in Mail.app and kept the old one in parallel. I tried dragging my emails from the old to the new mailboxes -- and just nothing happened.
2. I located the directory which contained my account’s mailboxes in the file system (
~/Library/Mail/V4/SOME-UUID
) and copied this as a backup. I then deleted the no-longer working email account. I used Mail.app’s import feature and was able to import all messages into a local mailbox. Yay. I then wanted to re-upload these messages to my **new** IMAP account and the following happened:
3. When dragging a mailbox’ messages (e.g. content of “Archive”) to my new IMAP account, seemingly all messages are moved to the server. But double-checking results shows: Only messages **WITHOUT** attachments are copied, and all my emails which had one or more files attached are simply lost (they no longer show up in the local mailbox either)
Is there any chance to clean up this mess and get my messages back on the server?
Observations about the backup so far:
* emails without attachments seem to be saved as .emlx
file
* in contrast, email with attachments are saved as .partial.emlx
qqilihq
(443 rep)
Jan 20, 2018, 04:50 PM
• Last activity: Apr 6, 2024, 04:21 PM
0
votes
1
answers
1272
views
The identity of "imap.gmail.com" cannot be verified
Has anyone come across this issue? [![enter image description here][1]][1] What is going on and how do you solve it? Is pressing confirm okay? This occurred when I went into MacBooks Notes app where I keep my notes. Here is some of the **Details** when expanded: [![enter image description here][2]][...
Has anyone come across this issue?
What is going on and how do you solve it? Is pressing confirm okay?
This occurred when I went into MacBooks Notes app where I keep my notes.
Here is some of the **Details** when expanded:


Daniel
(435 rep)
Aug 13, 2019, 04:59 PM
• Last activity: Apr 1, 2024, 07:24 AM
15
votes
6
answers
11634
views
Can I cancel this neverending message move in Mail.app?
A few days ago, I decided to move nearly 80,000 messages from an IMAP server to a Gmail server using Mail.app on Sierra 10.12.1:[![Mail.app Activity window showing two tasks: "Moving Messages, 4 of 79,718", "Checking for Mail…"][1]][1] [1]: https://i.sstatic.net/VzHOf.png This task still hasn't comp...
A few days ago, I decided to move nearly 80,000 messages from an IMAP server to a Gmail server using Mail.app on Sierra 10.12.1:
This task still hasn't completed.
"Checking for Mail…" comes and goes as one might expect, and normal mail functionality seems to work fine. Connection Doctor shows nothing strange.
However, this task has been going on for days, and moves _very slowly_—I've left the computer on all night and it only chews through a few thousand, occasionally stopping with an error. If I restart Mail.app (it takes a bit to quit), it eventually comes back up with the same 79,718 messages needing to be moved.
Is there any way to terminate this process? I'm inclined to try another tool at this point, but I'd like Mail.app to stop trying to move these messages.

Mattie B
(4561 rep)
Nov 18, 2016, 11:53 AM
• Last activity: Mar 12, 2024, 07:53 AM
1
votes
1
answers
369
views
Why won't my Apple Mail forward rule forward a Proton Mail email message?
On macOS 13.1 (Ventura) I have an Apple Mail rule that is setup to Forward a received email to a specific email address. In addition to forward, it will set the color of the message. I have tested the rule, and the message color is set, confirming the rule is firing, but it will not forward the emai...
On macOS 13.1 (Ventura) I have an Apple Mail rule that is setup to Forward a received email to a specific email address. In addition to forward, it will set the color of the message.
I have tested the rule, and the message color is set, confirming the rule is firing, but it will not forward the email. I have tried to use Forward, Forward with Message, and Redirect. None of these options will result in the email being sent to the designated address. I also tried different addresses, but still no luck.
I am using Proton Mail in this case, but I tried using Gmail instead and it works fine. So, it appears to be related to the use of Proton Mail, but I can't be certain.
> For those who aren't familiar with Proton Mail, they don't support email forwarding on their server and they require the use of a IMAP proxy app they call Proton Bridge, which encrypts and decrypts messages from an IMAP email client to the Proton Mail service.
Has anyone been able to get an email forwarding rule to work in Apple Mail and if so, anyone done so with Proton Mail?
Swisher Sweet
(5620 rep)
Apr 27, 2023, 10:58 PM
• Last activity: Jan 23, 2024, 07:04 PM
1
votes
0
answers
462
views
Apple Mail shows different amount of emails in inbox than server or outlook
I've found a post on the apple support community about this, but it had no solution. I have two inboxes in apple mail and outlook. One main inbox and one archive on a local NAS. The amount between Apple Mail, Outlook and the web client from the email provider (that should show the absolute correct a...
I've found a post on the apple support community about this, but it had no solution.
I have two inboxes in apple mail and outlook.
One main inbox and one archive on a local NAS.
The amount between Apple Mail, Outlook and the web client from the email provider (that should show the absolute correct amount of emails) is different. Web client and Outlook is the same, Apple Mail always shows less emails. I'm not sure if there are actually some missing, because the numbers are so big, it would take ages to test that. Grouping of conversations is disabled, although it seems even if it's activated, it doesn't reduce the number of emails shown at the top of Apple Mail. Some examples: **Folder 1 Exchange (Main Inbox)**
Outlook and web client: 10.442 emails
Apple Mail: 8.962 emails
**Folder 2 Archive on NAS IMAP (with bigger difference):**
Outlook and web client: 112.769 emails
Apple Mail: 90.563 emails
I've removed and redownloaded both inboxes in Apple Mail multiple times.
It seems Apple Mail shows the correct amount. Is there any way to fix this and show the actual amount of emails?
The amount between Apple Mail, Outlook and the web client from the email provider (that should show the absolute correct amount of emails) is different. Web client and Outlook is the same, Apple Mail always shows less emails. I'm not sure if there are actually some missing, because the numbers are so big, it would take ages to test that. Grouping of conversations is disabled, although it seems even if it's activated, it doesn't reduce the number of emails shown at the top of Apple Mail. Some examples: **Folder 1 Exchange (Main Inbox)**
Outlook and web client: 10.442 emails


Outlook and web client: 112.769 emails


It seems Apple Mail shows the correct amount. Is there any way to fix this and show the actual amount of emails?
jona
(261 rep)
Jan 11, 2024, 10:59 AM
1
votes
0
answers
28
views
Mails sometimes duplicated when recieved in Mail.app
On one of my Mac computers, when I receive an email that gets moved to another folder with Mail.app's filtering rules, sometimes I end up with two copies on the email: one in the intended folder, and another remaining in the root inbox. - It started last year with Ventura, but still happens with Son...
On one of my Mac computers, when I receive an email that gets moved to another folder with Mail.app's filtering rules, sometimes I end up with two copies on the email: one in the intended folder, and another remaining in the root inbox.
- It started last year with Ventura, but still happens with Sonoma.
- It happens only on one of my Macs, never with the others, the filtering rules being identical on all machines.
- It happens infrequently, not with every email.
- The mail box is standard IMAP (not GMail).
- Rebulding folders had no effect on this bug.
I haven't been able to solve this problem so far, so any insight would be welcome.
Miyase
(111 rep)
Sep 28, 2023, 08:09 AM
2
votes
1
answers
173
views
Why are sent emails not deleted when I delete a conversation in Apple Mail?
According to the [docs](https://support.apple.com/guide/mail/delete-emails-mlhlp1001/mac), when a conversation is deleted, `all of the messages in a conversation will be deleted`. Somehow, when I delete a conversation, sent emails are not deleted which creates orphans in the "Sent" folder. What am I...
According to the [docs](https://support.apple.com/guide/mail/delete-emails-mlhlp1001/mac) , when a conversation is deleted,
all of the messages in a conversation will be deleted
.
Somehow, when I delete a conversation, sent emails are not deleted which creates orphans in the "Sent" folder.
What am I missing?
sunknudsen
(1012 rep)
Nov 1, 2020, 12:47 PM
• Last activity: Sep 20, 2023, 11:42 AM
1
votes
0
answers
201
views
Can Apple Mail perform a server side IMAP search (and if so, how)?
I have a dovecot IMAP server that is configured with full-text-search, including Apache Tika with OCR support. This allows me to search within attachments, including image attachments. Using dovecot tooling, I can confirm IMAP search is finding text correctly within attachments. In a test account se...
I have a dovecot IMAP server that is configured with full-text-search, including Apache Tika with OCR support. This allows me to search within attachments, including image attachments. Using dovecot tooling, I can confirm IMAP search is finding text correctly within attachments.
In a test account set up for this purpose, containing various attachments containing known strings, Apple Mail returns zero responses to search queries I know do exist on the server.
The searches that do work appear to be the contents of a Pages document, but nothing processed on the server side.
Is it possible to tell Apple Mail to use server side IMAP search, and if so, how?
Graham Leggett
(111 rep)
Aug 6, 2023, 12:17 PM
1
votes
1
answers
580
views
Thunderbird deletes old messages without asking
I'm using Thunderbird 102.13.0. I recently noticed, that mail downloaded (via IMAP) to my Inbox, disappear, when they are more than 6 months old, and I really mean "disappear": They are not in the "Deleted" folder either. I checked the preferences whether there is a setting, which would purge automa...
I'm using Thunderbird 102.13.0. I recently noticed, that mail downloaded (via IMAP) to my Inbox, disappear, when they are more than 6 months old, and I really mean "disappear": They are not in the "Deleted" folder either.
I checked the preferences whether there is a setting, which would purge automatic messages automatically, but I could not find any.
What could be the cause of this behaviour?
user1934428
(1458 rep)
Jul 17, 2023, 05:03 PM
• Last activity: Jul 18, 2023, 01:03 PM
0
votes
0
answers
157
views
Can't connect to port 993 for a specific domain only
I have a strange issue on a Mac where port 993 is blocked for one site only. In Terminal I can type: nc -vz imap.gmail.com 993 and I get a succeeded message BUT nc -vz uk2.siteground.eu 993 fails and times out, yet nc -vz uk2.siteground.eu 443 AND nc -vz uk2.siteground.eu 465 Always succeed, so it's...
I have a strange issue on a Mac where port 993 is blocked for one site only. In Terminal I can type:
nc -vz imap.gmail.com 993
and I get a succeeded message BUT
nc -vz uk2.siteground.eu 993 fails and times out, yet
nc -vz uk2.siteground.eu 443 AND
nc -vz uk2.siteground.eu 465
Always succeed, so it's just one Port on that site. All works fine from other devices.
What has happened to my Mac, and how do I remove this block?
Travis Hiscock
(11 rep)
Apr 20, 2023, 12:52 PM
• Last activity: Apr 20, 2023, 01:23 PM
Showing page 1 of 20 total questions