What do you like best about Microsoft Outlook?
I’ve been using it for close to eight years, and it’s just become part of my routine. It feels familiar, and I don’t have to think about it much. Day to day it’s easy enough: search is quick most of the time, and the focused inbox keeps junk out so my client threads don’t get buried. Recall has saved me a few times inside our org when I hit send too fast. It also feels more reliable lately than it used to, although it won’t help if the email has already gone to someone outside the company. For client communication it’s solid—I don’t fight the app—and security-wise, sign-in is tied to our company account, so it feels locked down and sensible.
Getting it up and running on new machines has mostly been smooth. I sign into Microsoft 365, it pulls down my mailbox and calendar quickly, company policies kick in, and I don’t need to fiddle with much. Years back we did have a couple of profile hiccups and a massive OST that got cranky; I had to reset things and rebuild the index. It took a chunk of a day, but once it was done it stayed stable. Since then, updates roll in quietly and I just keep working. I’m in Outlook basically all day, five days a week—reading, writing, scheduling—so my usage is high, and it keeps up.
Feature-wise, there’s a lot I actually use instead of just ignoring. Rules and categories help me keep client work sorted, and delay send is a lifesaver when I want a second look. Shared mailboxes make teamwork simpler, and calendar invites drop in a Teams meeting so I don’t have to think twice. Attaching files from OneDrive is clean, and it turns the attachment into something that stays updated, so versioning doesn’t bite me as much. Search across years is good, though sometimes the index gets weird and I have to rebuild it—annoying, but not a deal breaker. Integrations are strong for me: Outlook plays nice with Teams and SharePoint. A couple of add-ins like CRM were hit or miss; one made things sluggish, so I removed it and it was instantly better. Support-wise, the official help pages and community posts usually get me unstuck. It’s not perfect, but it’s enough to move forward.
Overall, I’d definitely recommend it. It’s the most complete email and calendar app I’ve used on Windows, it handles client comms without drama, recall inside the org has bailed me out more than once, and the whole setup feels secure under our company account. It’s not flawless—no app is—but for day-to-day work it does what I need and stays out of the way. Review collected by and hosted on G2.com.
What do you dislike about Microsoft Outlook?
Time zones and recurring meetings can get weird. I’ve had a few double bookings because an update didn’t sync correctly to a shared calendar, or the meeting showed up late. Forwarding meeting invites to a client also isn’t always straightforward; sometimes people end up with two versions, or the attachment gets lost. The new Outlook direction versus classic adds another layer of confusion: buttons move around, some features seem to disappear, and I have to re-learn where things are, like Delay Send or Message Options. It’s fine once you settle in, but the constant changes still steal time.
Email recall is much better within the org now, but it can create a false sense of safety if you forget it won’t pull back something sent externally. I still double-check sensitive emails and often use Delay Send, because recall isn’t a magic undo. Sync on shared mailboxes can lag too; unread counts get out of sync, and it makes me think I missed a message when the cache just didn’t update. Review collected by and hosted on G2.com.
