Cannot activate Office Apps with High Sierra

Thank you so much for these screenshots and procedure. I spent the better part of today, going through each piece. I'm learning a lot (since I am not tech-saavy at all), and I honestly credit your descriptions and screenshots for helping me to stick with it, because normally I would have given up by now!

I still haven't managed to use the workaround. I'm not sure exactly what the issue is. It might be that I'm not sure which "older version" proxy tool to install that is compatible with my macOS Sierra version 10.12.6 -- I gambled and downloaded one that did open up a terminal with text that looked like this (I cut the top two lines with my data on it):

When I used this article to cross-check with your information: https://medium.com/ios-essentials/how-to-use-mitm-proxy-for-debugging-api-calls-on-macos-6bab9f78c909

it led me to this installation tip: https://docs.mitmproxy.org/stable/overview-installation/, recommending using Homebrew to install mitmproxy. Unfortunately, Homebrew couldn't be installed because MacOS 13 or later was required. I went ahead, hoping that the terminal I'd managed to open would be sufficient.

I enabled the proxy in the computer network settings just as you described (corroborated by that same medium.com article) but I did not see the tool showing flows in the Terminal UI.

I then attempted to install the tool certificates by starting mitmproxy (same Terminal shown above) and configuring my device with the correct proxy settings. I started a browser on the device, visited the "magic" domain mitm.it. but when I did the browser said "No Internet Connection". That's mainly where I stalled. I was following the proxy in the network settings just as described, but no luck. When I tried without those proxies selected, then I got the statement: "if you can see this, traffic is not passing through mitmproxy".

I then tried to install the mitmproxy CA certificate manually, using the guidance on this page: https://docs.mitmproxy.org/stable/concepts-certificates/ but couldn't figure out how. It's all above my skill level I think, despite having learned a lot trying. Or perhaps just my computer is that much older. Not sure if your macOS Sierra was older than the version 10.12.6? but that's the MacOS I'm dealing with.

I've been scrambling to get ready for a class I'm teaching on Friday and was hoping to use both Excel and Word for preparation and as screen-shares, but I might have to borrow someone else's computer to pull it off, since I cannot edit any Microsoft apps at the moment. Not in a position to buy a computer this week!

Anyway, THANK YOU for your help. I don't expect any more assistance, but thought I'd share my process in case anything super obvious was standing out to you (or others) that might be easy enough for me to try before I give up. Thanks again, and I hope others have success with your workaround. It certainly seems like a triumph over Microsoft that you managed to make it work for you!

Please look at the updated Gist, it should be easier to follow now.

Please take another look, just updated it with a better flow and some screenshots to help you validate the steps on your side (if you're curious, the system lang is Portuguese BR).

If anyone feels like it, it may be possible to write a mitmproxy add-on to quickly go through the redirection steps and avoid timeouts.

https://gist.github.com/rafaelfonte/56b9fb80daed8c586433e82859ccb876

Wow, this description is very much appreciated. I'm floored this week with the very same issue you're all describing and I'm extremely impressed with your workaround. If you're able to post screenshots, that would be amazing, as this is definitely above my skillset. Nice work!

Rafaelfonte22, that’s an interesting potential solution. I am, however, doubtful that it will work for those of us who subscribe to Office 365 because we do not get any sort of authentication code or product key but need to sign in to our Microsoft account from the app.

This solution works for the case you’re referring to. It involves authenticating to your MS account from the Office App itself by completing the sign-in flow in a web browser and then coming back to it with the code generated upon sign in. I’ll update the gist later with some images to help clarify the steps further.

Hey rafaelfonte22, a few tips/screenshots regarding what to look for within the mitmproxy window (Step 7) would be great please. Got it working easy enough, but the web requests appearing aren't jumping out at me in line with your github steps. Thanks in advance.