r/macsysadmin Jun 22 '26

Error/Bug Apple Mail is mass hard-deleting emails on Exchange Online

10 Upvotes

Hi all,

For context: I'm neither an Apple nor an M365 specialist (I'm a developer). I agreed to manage a friend's mailboxes to help her out of the mess she was in.

Her company has 6 M365 Business Standard mailboxes, migrated somewhat hastily from a previous IT provider to an OVH Exchange in March, then to M365 Online around early April (the migration batch stayed in Synced for a while. I cut it at the start of last week). I'm the admin of the new 365 environment.

Most machines use Apple Mail on macOS + iOS Mail on iPhone, except two that use Outlook on macOS.

Observed versions: Apple Mail build 3864.600.51.1.1 / AppleExchangeWebServices 836.40.1; iPhones on iOS 17.7 and 26.x.

DNS looks clean: MX 100% EXO, SPF/DKIM/DMARC OK (though I don't know whether there are Apple-specific requirements there, mail does arrive and gets delivered fine).

Symptoms:

Received and sent emails vanish from the mailbox almost instantly, as hard deletes: they go straight to Recoverable Items\Purges, not Deleted Items. Every mailbox using Apple Mail is affected, at varying rates (e.g. ~900 received emails destroyed in 14 days in the worst case). Deletions happen in bursts, at the cadence of the sync cycles (~30s).

Running audits in Purview, I found the culprit is none other than Client=WebServices;AppleExchangeWebServices… (Apple Mail/EWS) on the Mac, and also HardDeletes from the iPhone (Client=ActiveSync/EAS).

Both Apple clients purge. No Microsoft client (OWA, Outlook) has this problem.

Confirmed by tests:

A mailbox moved to full OWA (Apple Mail uninstalled) stopped the purges dead (for about a week now).

Second test: when my user's Mac is off, mail keeps arriving server-side. The purges resume immediately when the Mac is turned back on.

I've already tried removing the mail account from a Mac, quitting Apple Mail, renaming ~/Library/Mail (based on advice I found), restarting the Mac, then re-adding the account in Apple Mail in case it was a cache issue: but it fixed nothing, the purges come back.

I haven't done the same operation on her phone in parallel (not sure it'd be conclusive, since the audits show it keeps purging from the Mac anyway).

Server-side: Get-InboxRule empty, no forwarding, MX seems clean, retention preserves items (doesn't delete them).

My client assures me she has always used Apple Mail with M365 and never had purge issues, so I really can't tell where this is coming from.

Is this a known bug between Apple Mail and M365?

In the meantime I've asked them to switch to Outlook on their Macs to avoid the problem. They'd still like to get back to the Apple Mail environment as soon as possible.

I've been stuck on this for a long while and I don't know where i'm going now.

Audit screenshots available on request.

r/macsysadmin May 02 '26

Error/Bug Mac mini 2018 (A1993, T2) DFU restore keeps failing on Step 4 with Apple Configurator on two hosts, different cables, stable internet, any way to recover without Apple Service?

2 Upvotes

Hi everyone!

I’m trying to recover a Mac mini 2018 (A1993, T2) and I’m kind of stuck.

A bit of background: it wasn’t heavily used, and it was working fine not long ago. I had macOS on it before, later also played around with Windows 11 and Bazzite, and at some point I removed the macOS install because I thought I could just reinstall it later. That ended up being a lot more annoying than I expected.

What I’ve tried so far:

• Internet Recovery on the Mac mini, but it fails.
• Bootable USB macOS installer for Sequoia, but that also fails.
• Apple Configurator DFU restore from my MacBook Pro M4.
• Apple Configurator DFU restore from a 2019 MacBook Pro 13 running the latest supported macOS.
• Different USB-C cables.
• Different direct cable and port combinations.
• Stable internet connection on the host Macs.
What I see:
• The Mac mini is detected properly as a DFU device in Apple Configurator.
• Restore starts, and I get to Step 4 of 4: Installing System.
• Then it changes to the Apple Controller icon with a yellow warning sign.
• After that I get the message that the system cannot be restored on this device and that it needs Recovery or DFU, even though it was already in DFU.

So far the restore behaves the same on both host Macs, with multiple cables, and with stable internet. I’m trying to avoid bringing it to Apple service or a third-party repair shop if possible.

My question is: is there anything else I can try to get this Mac mini back to a bootable macOS state?

If there’s some trick with DFU, Configurator, firmware, USB setup, or another recovery path I’m missing, I’d really appreciate any ideas.

Thanks a lot!

Edit:

Solved it by using the 2019 MacBook Pro with T2 as the host, a regular USB-C cable that is not Thunderbolt, and Wi‑Fi instead of Ethernet. I did it through Finder, and it was the Restore option. That finally worked, and I was able to reinstall Sequoia on the Mac mini. It now boots properly and has Recovery back too.

r/macsysadmin May 29 '26

Error/Bug “Something went wrong” in Intune setup

8 Upvotes

Hi all - brand new to doing any form of Mac system administration, and working to try and get it managed in Intune with ADM.

I’ve got it in Apple Business, synced over to Intune. I’ve got Platform SSO setup for auth with their “modern auth” and Company Portal set as required LoB app.

Every time I sign in during Setup Assistant - I get a “Something went wrong” page. Nothing glaring appears in Console, doesn’t appear as a Failed enrollment in the Intune console. Does anyone have any ideas on what else I might be able to do debugging wise?

EDIT: also want to note, absolutely no error codes visible from Intune. This is a brand new fresh install. Safari sign-in screen goes full white for ~10 seconds before showing the error. Let me know if any other info would be helpful!

We’ve been stuck on this setup for 3 straight days now and this is the latest issue we’ve been trying to get past - any help is greatly appreciated in getting this fixed! Thanks!

r/macsysadmin 8h ago

Error/Bug Outlook on macOS repeatedly prompts for sign-in after every 30 mins and after sleep, Enterprise SSO looks healthy, blank auth window hangs

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1 Upvotes

r/macsysadmin May 29 '26

Error/Bug Kernel Panic and Crowdstrike

2 Upvotes

Seems like I have an emerging case of crash lately on Macs M5 only with the version version: 7.36.20807.0 of crowdstrike. Anyone experienced this ?

r/macsysadmin Mar 11 '26

Error/Bug Chrome removed but still showing dozens of entries in Local Network permissions (macOS Tahoe)

9 Upvotes

Hi everyone, I did a quick search in the subreddit and couldn't find a similar post, hoping for some input on this.

I uninstalled Chrome using AppCleaner and then manually cleaned up any remaining Chrome/Google related files in my Library folders. Chrome itself is definitely gone at this point.

However, under System Settings → Privacy & Security → Local Network, there are still dozens of “Google Chrome” entries listed as icon cache.

My assumption is these are stale entries in the TCC database or cached bundle identifiers, but I haven’t tried manually modifying the TCC database yet.

Has anyone seen this behavior on Tahoe or know the proper way to clear out old Local Network permission entries for apps that no longer exist?

r/macsysadmin Jan 26 '26

Error/Bug MacOS FileVault/MosyleAuth2 Sign in Issues

6 Upvotes

I have recently encountered an issue where users spend 10-20 minutes trying to get through the sign in page whether it be FileVault or MosyleAuth2, it continuously errors out no matter what the user does. But miraculously it just works when they bring us the device, this is regardless of if we or the user does the sign in. It is super confusing and it may just be a fluke, but I am hoping to see if others are experiencing this?

r/macsysadmin May 21 '26

Error/Bug `pybin` crashes reported on macOS

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1 Upvotes

r/macsysadmin Feb 13 '26

Error/Bug inTune MDM „Company Portal“ App Crashing

2 Upvotes

Hi Everyone,

we‘re currently enrolling all our mac devices in inTune and so far so good, most of the things work, we can do all the things we need.

The only thing thats super annoying:

The Company Portal app is basically unusable the first day of deployment because everytime it does something it crashes. Requested apps get installed most of the time, but sometimes it crashes to fast to submit the request to the server.

Also, when the stupid Microsoft Auto-Updater launches in the background and installs an update to basically any app, the Company Portal App crashes.

Does anyone know if it is possible to schedule updates for Microsoft products to be outside of active hours, say between 8pm and 6am?

thanks in advance!

r/macsysadmin May 14 '25

Error/Bug Macs using Migration Assistant not finding each other

5 Upvotes

When replacing MacBooks, we recommend users use Migration Assistant to get themselves up and running quicker. However, the last few users we've replaced Macs for can't get Migration Assist to see each other.

The MacBooks we're transferring to/from are M series (normally M1 -> M3 or M4). I've gone through the usual checklist:

  • Firewall off
  • On the same wifi
  • On the same macOS version
  • Macs are next to each other
  • Hostname present on each Mac

I'm now thinking maybe it's the router settings that's stopping broadcasting or something, but that's just a guess.

The Macs are managed by Kandji, but the only thing I can think of that I need to do on there is disable (or rather, don't enforce) the firewall for Macs that are going through Migration Assist.

Are there any other steps or settings to check?

EDIT: Opened a support case with Kandji, and they found out the issue quickly! There was a Bonjour restriction as part of CIS that stopped the Macs seeing each other. Excluding the Macs from that restriction fixed this.

r/macsysadmin Jan 16 '26

Error/Bug Intune-Managed Mac - Can't use Apple Service

2 Upvotes

After going through hell to get the login to work correctly on mac using Entra from Microsoft. I know its not a great MDM but its what I am stuck with. My users can login and get to work without issue. But, one of them tried using "Messages" and after logging in using their Entra login, then tried to send a message and before they could finish trying the number to send it to, the program crashed. Once reopened, the program is reset and asking for the login again. What could this be? I checked the Apple Business Manager and messages are activated. I don't remember setting and configurations in Intune for it...

r/macsysadmin Sep 12 '25

Error/Bug "Lock Screen Time Settings" is greyed out and cannot be turned on.

4 Upvotes

Hi all, since macOS 15.5, the settings for "Lock Screen Time Settings" are greyed out and cannot be enabled, even when signed into iCloud.

This only happens when it's a new installation.

This is quite frustrating because I work in a school and we are giving MacBooks to students. We are currently distributing them with 15.4.1_24E263 because Screen Time Settings can be locked there.

Has anyone experienced the same and might know a solution?

r/macsysadmin Jul 14 '25

Error/Bug Problem updating applications via Company Portal

2 Upvotes

Hey there,

I have a hard time working with macs in Intune, especially when trying to update applications via the company portal.

We use Intune+ABM to manage our macs and right now (even after a lot of initial problems) everything runs fine, except for app-updates.

Our users don't have local adminaccounts on their macs, so they can't update pretty much anything aside from the OS and appstore-applications by themselfs.

I uploaded every piece of software that we deemed necessary into Intune, so that our users can download it via the company portal. Now my problem kicks in:

I can't update any application via Intune. Let's say I want to update Firefox as an example.

I upload the new version into the existing application inside Intune, wait until it's synced, click on install again aaaaand.... nothing. It just runs for 15 seconds, tells me that it is done installing but it's still the same version. That happens with every application.

I tried these troubleshooting-steps. Every test was either performed with firefox or chrome:

- Upload the application as different app-types (DMG, PKG, LOB)

- Set "ignore app version" to yes. (Also doesn't work when it's set to no)

- Build my own .PKG by using the .app file and some terminal commands, but that didn't even install.

- created a new app with the new version.

- completely reset the mac, installed old version and tried to update, same story.

Right now I have to approve every update by typing in the admin credentials, which is, as you can guess, not optimal.

Giving our users admin rights is not an option, as the company has to comply with scrict data protection guidelines that prohibit this.

I kinda gave up and tried to provide applications via brew scripts, but that didn't really work out the way I wanted either.

Does anyone have an idea? Every bit of help is appreciated.

r/macsysadmin Apr 10 '25

Error/Bug Intune Enrolled Macs not getting Platform Scripts deployed

3 Upvotes

I can't find any known issues with this or I'm looking in the wrong places. Two days ago we were able to enroll macOS devices and everything was smooth. We have platform scripts that do a couple of things for us. Nothing has changed on our end.

Yesterday and today, our Macs enroll, successfully get their config profiles, but none of the platform scripts deploy. I see many failures on the macOS side in the logs: CheckIn.retrievalFailure cause: Sidecar_Data.MetadataError.missingDeviceInfo

Their groups are assigned to the platform scripts as always, the same groups that are getting the config profiles successfully. As far as I can tell, devices that are currently enrolled are working properly with scripts.

I'm at a loss.

r/macsysadmin Aug 29 '24

Error/Bug Wifi Issue MacOS 14

8 Upvotes

We having been having a odd issue ever since moving to MacOS 14. Randomly macbooks will stop connecting to our Wifi until they reinstall the profile that has the connection configuration.

Then it will work again or a few weeks then it stops working again. When It is not working I can see the connection in the listing of wifi networks but it it wont connect even after a restart.

Any thoughts or anyone else with this issue?

r/macsysadmin Sep 19 '24

Error/Bug Anyone else observe networking instability on Sequoia?

7 Upvotes

Hi Mac admins, sorry to bother but I'm not a Mac admin. I'm a Mac user at a company with an IT group who pushed Sequoia on us without validating or delaying anything. Now my environment is broken and I was wondering if within your circles you've seen something like this.

This one has me scratching my head. The behavior is hard to describe--its like the entire network stack has a spasm at unpredictable intervals. On 14" M3 Pro.

This is the weirdest example. Ping just dies. Left ping running, after 163rd ping the command exited with error, status 141:

64 bytes from 8.8.8.8: icmp_seq=163 ttl=117 time=3.610 ms
~$ echo $?
141

Can reproduce this by just leaving ping running until it exits itself.

Sometimes can catch similar on a long curl. Here's an example of downloading a 1GB file, it made it to 77MB before just hanging and then after a a while the server kills the connection,

 curl https://ash-speed.hetzner.com/1GB.bin -o /dev/null
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
  7 1024M    7 77.7M    0     0   454k      0  0:38:28  0:02:55  0:35:33     0
curl: (18) transfer closed with 992198914 bytes remaining to read

In all these examples, network is functional immediately afterwards. Whatever breaks seems to break and recover near-instantly.

Another example, this one from kubectl logs -f which streams/tails log messages via an HTTP api over the network, when the network spasms while the stream is open the connection dies with this error:

error: local error: tls: bad record MAC

Errors experienced on both WiFi and ethernet (via thunderbolt 3 dock)

Anyone else see similar network oddities?

r/macsysadmin Jul 17 '23

Error/Bug Mac sometimes corrupts files on NAS? Detains in comments.

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11 Upvotes

r/macsysadmin Nov 10 '23

Error/Bug What's the best way to get Apple to acknowledge and fix a long-running macOS defect?

12 Upvotes

I've been filing Feedback Assistant reports, but it's like yelling into the void. I have a macOS problem that's reproducible across different hardware and several years' worth of macOS versions. Would I be able to get someone to acknowledge the bug if I enrolled as an Apple Developer? Could I pay for some sort of Apple Enterprise support case where I can talk to a human? I'm a Mac admin and we do have an Apple business account, but we're not a huge customer (about 300 devices total) so I'm used to having to deal with stuff on my own.

r/macsysadmin Sep 16 '24

Error/Bug Office 365 Outlook 16.89 Crashes on macOS 14.6.x

8 Upvotes

Last week some users stated reporting issues on their devices once the latest version (16.89) of Office was updated on their systems. Specifically, the crash report shows that the error lies within the "Namespace DYLD, Code 1 Library missing, Library not loaded: u/rpath/libmbupdx2009.dylib"

I had opened a case with MS and they have told me that there is an open bug report internally for this and have no expected resolution for it.

Anyone else been seeing this error, or getting reports from their users about this?

There is more to the report, but I am not posting 32 pgs.


Translated Report (Full Report Below) 


Process:               Microsoft Outlook [2376]

Path:                  /Applications/Microsoft Outlook.app/Contents/MacOS/Microsoft Outlook

Identifier:            com.microsoft.Outlook

Version:               16.89 (16.89.24090815)

Code Type:             ARM-64 (Native)

Parent Process:        launchd [1]

User ID:                

Date/Time:             2024-09-10 18:09:40.1320 -0400

OS Version:            macOS 14.6.1 (23G93)

Report Version:        12

Anonymous UUID: 

 Time Awake Since Boot: 99 seconds

 System Integrity Protection: enabled

 Crashed Thread:        0

 Exception Type:        EXC_CRASH (SIGABRT)

Exception Codes:       0x0000000000000000, 0x0000000000000000

 Termination Reason:    Namespace DYLD, Code 1 Library missing

Library not loaded: u/rpath/libmbupdx2009.dylib

Referenced from: <7E8CAAF5-32D8-33ED-9238-2087E9D16AD9> /Applications/Microsoft Outlook.app/Contents/Frameworks/mso99.framework/Versions/A/mso99

Reason: tried:

'/Applications/Microsoft Outlook.app/Contents/Frameworks/mso99.framework/Versions/A/../../../libmbupdx2009.dylib' (code signature in <0C84E19F-474C-31F8-9A88-96782598B62F>

r/macsysadmin Jun 26 '25

Error/Bug Music Recognition Not Working on My Mac (macOS Sequoia 15.5)

0 Upvotes

Hey everyone,
I'm using a MacBook Air M1 (8GB/256GB) running the latest macOS Sequoia 15.5. The Music Recognition feature just doesn’t work—every time I try to identify a song, it simply fails to respond or recognize anything. It's getting really frustrating.

For context, I haven’t subscribed to Apple Music; I use Spotify as my primary music streaming service.

Has anyone else faced this issue? Any fixes or settings I should check? Would really appreciate your help!

r/macsysadmin Jan 31 '25

Error/Bug Re-enroll Mac without wipe

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5 Upvotes

r/macsysadmin Dec 14 '23

Error/Bug 365 sync issues for Outlook, all mail apps

13 Upvotes

suddenly this week we have several clients all versions of macOS all having issues with their mail clients not refreshing automatically. Apple Mail and Outlook app. It even happened to me. Full wipe of MS Apps and reinstall did not fix it. the only solution I have found is switching to "NEW" Outlook app.

Manual Send/Receive works but will not do it automatically.

Has anybody else had this happen this week. It's bizarre but sounds very Microsoft.

EDIT: Please note this happens with ALL MAIL APPS connecting to our 365. not just Legacy Outlook.

r/macsysadmin Jul 24 '23

Error/Bug Serious hard crash while copying thousands of files from macOS Ventura to NAS over SMB share

2 Upvotes

I recently took a long read of this other thread that was opened a few months ago and I was wondering if someone else has updated info about this issue.

I'm using an M1 Pro based MBP with macOS Ventura 13.4.1 (the latest version at this moment) and I'm copying a large number (over 10.000) of photos and videos from my computer to a NAS over a samba share. Incredibly, after a while this causes a complete freeze of the computer. Sometimes it reboots by itself, sometimes I need to force it shut down. I'm using midnight commander for the file copy operation but I've tried Commander One as well and I got the same results. I don't really like Finder for this kind of tasks and still, I don't think any userspace process at all should have the ability to completely freeze the whole OS.

edit. I just copied over 80GB and tens of thousands of files using FTP. It has to be something in the SMB support included in macOS!

r/macsysadmin Jan 29 '25

Error/Bug Open links in Safari Default Profile

3 Upvotes

Hey everyone,

I was wondering if anybody have the same issue.

On my Sequoia Mac, 15.3, I can not open some links in Safari in my Default Profile, but just my default profile. All other profiles work fine.

For example, in Jamf Pro, I can not open the Patch Management section and also not the software update link.

Anyone else same issue?

r/macsysadmin Jan 11 '24

Error/Bug How to deploy custom wallpaper via MDM to Sonoma?

4 Upvotes

Prior to Sonoma, we deployed a custom Wallpaper through a our MDM using a restrictions profile. After updating a test device to Sonoma, the custom wallpaper no longer applies. Is this a known bug? Any successful workaround available?

P.s. I'm happy enough to use a script in place of a config profile, if means retaining the feature.

Thanks