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    • #540965
      Michael Pietroforte
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      I just had an issue with Outlook 2016 (Mac version connected to Office 365) where emails and tasks were disappearing randomly. I used the support tool integrated in Outlook and someone from Microsoft responded almost immediately (amazing!).

      Support recommended to reindex with the OutlookSearchRepair tool and the missing items reappeared. I am unsure if this really solves the problem because I believe that something corrupts the index regularly.

      I just wanted to share my positive experience with Microsoft’s Outlook support. A few days ago I had an issue with free Outlook app for iPhone and support was just as fast.

      The OutlookSearchRepair tool with a few other useful troubleshooting tools can be found here.

      What is your experience with Microsoft’s support lately?

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    • #543297
      Paolo Maffezzoli
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      4sysops member of the year 2018Member of the Year 2019
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      I don’t have any recent experience about Microsoft support. Btw, interesting to know the OutlookSearchRepair toolfor Mac. If can help, when I had issues on Outlook for Windows, I have run the Inbox Repair tool for Microsoft Outlook 2016 and it worked fine and solved my problem. (link)

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    • #544725
      Michael Pietroforte
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      Paolo, thanks! I didn’t know about OutlookSearchRepair. In the past, whenever I had an indexing problem with Outlook, I just removed the mailbox and added it again. This always solved the problem. However, this time rebuilding the index only was a temporary solution. After I rebuilt the index all items reappeared. However, on the next day two new items disappeared. This is definitely a serious Outlook bug. It is quite disruptive if you can’t rely on your task lists. If you have a large task list and only 1 or 2 disappear, you probably notice it too late.  Let’s see if I can convince the support team that this is really a bug.

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    • #599379
      Michael Pietroforte
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      Microsoft support now confirmed that it is an Outlook bug. It took me more than a month to persuade them with almost daily conversations.

      In the end it turned out that they were testing with an outdated macOS version even though it was clear right from beginning that the cause of the issue is an incompatibility between Outlook and macOS. Outlook search depends on Spotlight which indexes Outlook items.

      Everyone running High Sierra is affected by this serious Outlook bug. It makes items such as tasks and emails with a due date disappear. I am pretty sure many Outlook users around the world will miss important deadlines. It has been more than a week now that Microsoft confirmed the bug and more than a month since I reported the issue, but still no fix.

      It is hard to believe that Microsoft’s support knows so little about IT troubleshooting. The first thing support has to make sure is that everyone is on the same OS version. And how come that Microsoft is forcing everyone to update Windows, but their own staff works with outdated OS versions?

      I am already looking for another solution now and I will soon dump Outlook and Office 365. There are many better solutions for the Mac. I’ve been using  Outlook 2016 since its release and I am very tired about its unreliability. I’ve downloaded terabytes of updates from Microsoft. So far not one useful features has been added and with every new update you have to be afraid that new bugs are added.

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      • #599821
        Bryce McDonald
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        Outlook instability on Macs has always been a problem imo.  What was most frustrating were the old iOS calendar bugs where if you accepted a meeting from iOS it would spam the entire attendee list with a whole bunch of “meeting accepted” emails.  The issue was more topical than anything, but it was a big annoyance to say the least.  Unfortunately, there are few systems that are as robust as Exchange at an enterprise level.  Yes, there’s Lotus Notes and Domino servers, but they’re riddled with just as many bugs as Exchange except there’s 1/10th the number of articles out there to help administrators.  The other option would be to change your enterprise to GSuite, but the administrative options there to either left-click and manually enter everything, or interact with complicated API’s.

        You mentioned better solutions than Outlook for Mac – do these solutions still support Exchange?

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        • #599865
          Michael Pietroforte
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          Bryce, you should have told me that 3 years ago when I moved from Windows to macOS. 😉 I wanted to keep working with Office 365 and I was quite happy when Microsoft released Outlook 2016 right after I received my Mac. If I only knew better…

          The first release was so full of obvious bugs that it was clear to me that nobody seriously tested Outlook before the release. For instance, the smart folders were not working at all. I thought, okay, this is Microsoft. In the next release they will fix this. They didn’t. It took them 3 or 4 releases until the smart folders finally worked. It is just that with every release new bugs were introduced. Many of the minor bugs of the first release haven’t been fixed until today.

          I think this entire strategy to embrace other operating systems than Windows is failing. Microsoft is obviously unable to hire the right people. I mean what kind of macOS or Linux expert really wants to work for Microsoft?

          You are right, Notes/Domino is no match for Outlook/Exchange. I think large enterprises don’t really have a choice. There are no alternatives to Exchange/Office 365. However, things are different for small and mid-sized organizations. Since Exchange can now only be managed with PowerShell, it is no longer an option for companies who can’t afford to hire an engineer just to manage their email server. Those organizations either move to Office 365 or G Suite.

          I think small and mid-sized organizations don’t really need to “automate.” After the mail system is up, they add a new user every once in a while and that is all the administration that needs to be done. Every secretary can do that.

          As to the Mac, search for ‘mac best email client.’ You will notice that Outlook often is not even mentioned in comparisons. And yes, Exchange also doesn’t really matter on the Mac. If you really need it, you can use the built-in mail client. It is very reliable and has all features that most users need. The Mac calendar app is better than Outlook and also syncs with Exchange. I love the Mac Notes app and I like it even better than Evernote. It also syncs with Exchange. The only weak app is Reminders. It can’t really replace Outlook tasks. But it also supports Exchange.

          As far as I am concerned, I am planning to dump Outlook and Office 365. I am also unhappy with OneDrive which has it own problems on the Mac. I regret that I moved from Dropbox to OneDrive. I think if you are working on a Mac, you want to avoid Microsoft as much as possible. I will still have to stick with Skype for a while. But I think it is fair to say that Microsoft totally messed up Skype which was really a great app before Microsoft took over.

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    • #807002
      Michael Pietroforte
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      Hard to believe, these are my first days without Outlook for ages. (I’ve been using Outlook since the very first release.)

      I am currently testing a combination of Apple Mail (connecting to Office 365) with Daylite, a great CRM application for macOS/iOS that integrates itself well in Mail, Contacts, Calendar and Reminders of macOS. All I can see at this point is that I am so thankful that Microsoft still didn’t fix this serious bug after months even though Microsoft’s official Outlook support can reproduce the flaw.

      Without this bug I would have never made this move. Apple Mail is so much better than the mail component of Outlook. It is amazing how thought-though this application is. The same applies to Daylite which is incredibly well-designed and which I now use for my contacts, tasks, calendars, and much much more.

      I literarily boosted my productivity by dumping Outlook.  Thank you Microsoft!

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    • #820289
      Aiden Bill
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      I too had to suffer due to unavailability of image attachments in my emails. Microsoft support didn’t seem to much help. I had to work as per this suggestion from the Apple Support forum:
      https://discussions.apple.com/thread/8415861

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      • #820292
        Michael Pietroforte
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        Post count: 1852
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        Aiden, Outlook is very unreliable. I rebuilt the Outlook database numerous times from backups and from Office 365 because of all kinds of bugs. It is only a matter of time until you run into the next problem. The last thing you want is to continuously fight with your mail app. Give Apple Mail a try. It is not only much more reliable, it also much better thought-through.

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    • #820296
      Aiden Bill
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      Thanks Michael. I am Looking forward to it. My colleagues have been using Apple Mail for long and its time, I shall move on too.

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    • #820318
      Aiden Bill
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      Hi Michael,

      I think it is the issue with the IMAP server only, and not Apple Mail or any other email client.

      I tried out Apple Mail and the same emails wee again without any attachment.

      But i read this one from the official Apple Discussions forum. The sufferer claims that worked. Does any one have had tried it before:https://discussions.apple.com/thread/8571445

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      • #820321
        Michael Pietroforte
        Keymaster
        Post count: 1852
        Member Points: 23,714
        Author of the year 2018
        Rank: Level 4

        What email provider are using? Maybe you can access the emails through their web interface? If the emails are not on the server, you can rule out that it is a problem of your email client.

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