I have been using Apple Mail on my Mac and iPhone to access both my work Office 365 account and my personal Gmail, with a unified inbox. I like it - it mostly just works, and provides a clean experience. But yesterday I had a mini-crisis where I discovered that an Office 365 mail that showed as sent on my MacBook – had in fact NOT been sent via the server or otherwise. No error message - no nothing, Just a silent fail that I only discovered through manual sleuthing.
This has, of course, triggered a 24-48 hour meltdown where I have switched everything to Microsoft Outlook, hated it, gone back and between new outlook and old outlook, found myself thinking of going back to Apple Mail even though I have experienced the send failure, etc.
Someone help me – is Apple Mail mostly reliable for Office 365 and I am overreacting? Or do I need to face the reality that Outlook needs to be used for Office 365 rock-solid consistency?
Interested in the answers here. My company is about to switch to Office 365. I’ve used Apple Mail with my current work Exchange email for years ,and it has been solid. Now you have me nervous.
We have used Office 365 at work for several years now. I’ve used it on the various MacBooks I’ve owned and, to the best of my knowledge, not had an issue with messages sending from the Mac and not showing up in the sent folder on a work PC, or via the O365 web interface.
The only issues I have had with mail sending are when the internet connection to the site has failed. At this point no messages can be sent, and I do get messages stuck in the local outbox which need to be copied and sent once the internet connection comes back up. As I know the internet has gone down this is something which I am aware of, and not something which fails without warning. The outbox folder has a number next to it (and appears in the sidebar of mail) when a message is stuck to there.
Not everyone is allowed to access their corporate email with alternate apps or devices. But even if one has that permission, there is no one who can give you guarantees of perfect interoperability.
Do you use Apple Mail on other devices, are those having similar issues recently? Only reason I ask is that the Exchange admin can block access to non Outlook clients, though you should get an error if they enabled that. Just thinking of what could have changed. Since exchange is all hosted, you should delete account from Mac and re add it. That should be where you see if it’s disabled.
Here is an example of how MSFT allows this on mobile. You can do desktop version as well.
If access visa non-Outlook clients was disabled, you’d be getting sync errors regularly and wouldn’t be receiving new emails. It’s be obvious, not like this with a single email not being sent.
Did you verify that the message(s) had not been sent by logging into the server using webmail?
There were several times over the years that I had users say that they had not received an email, or that messages had gone missing, etc. When the problem was their email client just wasn’t accurately showing them what was in their account.
You may indeed have a problem but, IMO, the only way to know for sure is use webmail to look at your messages on the server.
@FTLFTR If the email shows in your Sent items, it WAS sent, otherwise it would be sat in an outbox.
@WayneG is speaking from his vast experience of supporting system users, I concur with what he’s saying (using my vast experience of supporting id10ts, errr system users). In the majority of cases where someone says that they “never received an email” they accidentally deleted it, filtered it off with a rule or even just lost it in the other 300 emails they received that day.
Why oh why do people not unsubscribe from emails they’re never going to read. Stop me before I start on people who don’t manage their comms and have 10,000 unread emails in their inbox, can you imagine that happening in a physical inbox…
The OP didn’t mention what versions of macOS and iOS were installed, but with both Sequoia and iOS 18 I’ve had recurring issues with Gmail. The account logins drop, or all the mail (IMAP) is not downloaded, etc. I know this is Gmail nor M365 (or O365), but the symptoms described above seem to be parallel. I generally rely on Gmail in Chrome now, instead of Apple Mail.
My “vast experience” also taught me that missing emails are frequently found in the folder above, or the folder below, where the user says they filed them.
Most technically savvy employees can tell a story of when a corporate VP called them in for help because a Windows Outlook mailbox was full. (Two gigabyte file size limit at that time.)
We once had a user who “needed” to retain everything, and (at a time when a standard on Prem exchange server database had a limit of 75GB) was using the majority of a server just for their mailbox. I’m talking 10 year old emails with attached reports from a system which had no use to an organisation which was (financially talking) 20 times larger in turnover in that 10 years.
When we told him that in the event of a Server failure, it would take approximately 10 days to restore the backup so he could have full access to his mailbox and he literally went white. At that point he suddenly got a lot more sensible and in 2 hours his mailbox was less than 1/4 of it’s previous size. We then set him a limit so that he could’t increase it significantly in size or he wouldn’t be able to receive emails.
yes sir - that was the “sleuthing” I described. Not sent on my iOS app. Not sent on the server (going to outlook.com). Only showing sent locally on my MacBook.
As for MacOs - why use either Apple Mail or Outlook? Why not simply use it as webmail instead?
Office 365 can accomodate notably large mailboxes - up to 50Gb or 100Gb depending on your subscription. Especially if you have multiple computers it can be a considerable effort to sync them all. And even if you do keep Mac Mail or Outlook up to date, there is a good chance Outlook Web will be notably quicker at searching for content than Outlook for Mac or Mac Mail.
That aside - MIcrosoft 365 Outlook Web has very convenient integration with OneDrive which lets you send file attachments either as traditional attachments as hyperlinks to OneDrive. The Hyperlinks are particularly useful for the attachments to remain usable as you later reply or forward messages in a chain.
What benefits do you see from using Mac Mail or Outlook for Mac rather than web-based Microsoft 365 email?
I am old school and have just always preferred dedicated apps, which I can automate certain things with things like Keyboard Maestro, Better Touch tool etc. But you’re right - there is a lot of issues avoided by simply using the web apps. I have already decided I will lose unified inbox because I probably need to use Outlook app to access my Office 365. Once that is lost, maybe I should give the web apps a go…
If you use webmail for incoming email you can still create automations to save email in Macos apps. Example here:
For outgoing email, you can still configure Mac Mail if you want - I am simply suggesting you configure Mac Mail to retain only a very small number of messages. You can do a quick check of your inbox if you wish on Mac Mail and can still send outgoing email as you wish from Mac Mail; I am simply suggesting to not keep your main email archive locally and to handle any mail rules on the web.
