Google Inbox/Calendar vs Outlook

I have not had an easy time adjusting to Google Apps. GMail is ugly, Inbox is pretty but severely limited and Google Calendar is deeply frustrating. More and more, I have been missing the power and elegance of Microsoft Outlook. I decided to try and use Outlook on top of Google Apps.

At first, I tried to configure the settings manually. This failed spectacularly. Interestingly, I got this passive aggressive email from Google. Notice the language:

Someone just tried to sign in to your Google Account from an app that doesn’t meet modern security standards.

We strongly recommend that you use a secure app, like Gmail, to access your account.

Google just called Outlook insecure, even though it was using SSL. It blocked login without giving me any way to allow it. Ballsy move Google.

Luckily, another division of Google made the Google Apps Sync for Microsoft Outlook. Brilliant little piece of software. It created the proper profile and logged me. It needed to ask permission to connect. This is what I saw:


That is a metric crap-ton of permissions to be asking. I have never seen so many requests in one app. Outlook is big, but DAMN.

After syncing everything down, it seems to be working. A weight seemed to be lifted off of my shoulders. However, I know this isn’t going to be perfect. I am not going to get free/busy scheduling without going into Google Calendar’s shitty interface. The mobile integration favors using Google, not Outlook. I am also not sure how folders will be interpreted by Google. The Inbox grouping in Google is not represented in Outlook.

Ultimately, this is a mess.

For anyone starting up and choosing, I would suggest Microsoft 365 rather than Google Apps. The reason is that I think it’s a better UX. It shouldn’t be a question of brand, it should be purely a UX question. Microsoft on this score wins hands down.

Well, no use crying over spilled milk under the bridge. Worst case scenario, I get rid of Outlook and go back to Inbox/calendar.

One reply on “Google Inbox/Calendar vs Outlook”

I use gSyncit to connect my outlook calendar to my google calendar, which works very smoothly back and forth. It has a free version, but the paid version is only $20. I still find it amazing that there are so many features for both Office and Google that are done by 3rd parties. For example, can’t google calendar have an reasonable export feature built it. I assume there is a whole team that works on google calendar, and I wonder what they are doing on a daily basis.

Whatya think?