I wanted to make a note of a number of changes I am unhappy with. First, whenever there is a typo (red line underneath a misspelled word, etc.) used to I would right click and then easily select the correction. NOW, right click does not work for this but rather it wants a left click. Whenever I click the left click and then the drop down comes with the guessed corrections it almost NEVER works when I click it… The update is much slower and works about 50% of my 1st attempts…Second, the new attachment feature in new drafts is completely unnecessary and unwanted. Now, when I go to drag an attachment to my email I almost always attach it on the left side which now no longer just attaches the attachment file, it converts to a text link attachment in the body of the email. This is frustration, because I will NEVER need this feature and it disrupts my workflow multiple times per day. There are so many unwanted changes each time you put out an update to Outlook. I don’t know why Microsoft feels like there needs to be changes so often and “fixes” to things that were not problems or issues to begin with. This is incredibly frustrating to businesses and organizations who are used to processes and functionality and then have to learn a new way that is genuinely less efficient and aggravating. I know Gmail does not change functionality this dramatically and often.

Where do I start, the Outlook app on Mac is so limited. There are a ton of things that you have to use the online version just to perform or configure. If you're used to Outlook on PC and you switch to a Mac, it's even more frustrating. I wanted to have a group of contacts that I can easily send emails to on a regular basis and figuring this out on Mac was so darn hard. I created a 'Group' thinking this was the right thing to do only to find out that there is a difference (on PC) between 'Groups' and 'Contact Groups'. After Googling and racking my brain, I find out that 'Contact Groups' are known as 'Contact Lists' on Mac. If you create the contact list (which you have to alter a setting in preferences just to have that option), you can't see a list of your contact lists unless you use the web browser version. If you maximize the window, you can't create a new email or pop out an email into an actual new window. It'll show up as an immovable pop up that covers the main window. When trying to route my Outlook mail through the Apple Mail App on my iPad, there's a bug that won't allow me to sign in to my Microsoft account (I'm able to do it on my iPhone) thereby not allowing me and of course it is impossible for me to get in contact with some type of customer support. And there are so many more examples. Overall, they're not spending enough energy into optimizing the Outlook for Mac app, the UI can be quite overwhelming, they try to mimic PC functionality in ways that don't work for the Mac context, and good luck trying to get in contact with customer support. If you are a Mac user and aren't required to use Outlook...RUN! Use something else.

The core functionality of this app - to reliably send and receive emails, calendar appointments, etc. - has never faltered. However, there are many bugs that need fixing. One prominent bug is formatting inside of emails. Attempting to change fonts, styles, add bullet-points, indentations, etc. almost always results in the program failing to make theses attempted edits, and the program itself often slows and beings to glitch here as well. Another issue is when I need to search for an email thread - I can enter the entire subject line from the thread - word-for-word, character-for-character - and the search results frequently pull up completely unrelated threads first in the search, with the thread I’m looking for being anywhere from 5-30 search results from the top. Sometimes, the thread will not populate in search results at all, and I’m forced to restart the app to begin the search again.There are other, smaller bugs. Again, the app’s very basic core functions are generally never compromised or unusable. Most of the issues are found in the non-essential features, which make working with this program on a daily basis frustrating.

I really wanted to like the new Outlook for Mac. The built-in AI and Copilot features are genuinely helpful and are the only reason I’m giving this two stars instead of one. They show real promise. But almost everything else feels like a step backward.The biggest problem is the workflow around flagged emails. Outlook pushes you toward Microsoft To Do as the place to manage them, but To Do doesn’t show the full message chain. You only see a tiny slice of the conversation, which makes it impossible to act on anything meaningful. That alone breaks a core email-processing workflow I’ve relied on for years.On top of that, category keyboard shortcuts—one of the fastest ways to triage emails—are completely gone. Finding flagged emails is harder than it used to be. And the interface itself looks strangely cartoonish, almost like a simplified mobile app instead of a professional desktop client.In the end, the new Outlook looks modern, but it removes too many of the power-user features that made Outlook efficient and reliable. Until Microsoft brings back full message-chain visibility in To Do, category shortcuts, and better flagged-email handling, this version feels like a downgrade, not an upgrade.