A poor Outlook
As someone having used GSuite for many years at work, I guess I can call myself a GMail power user. I was dismayed as a decision was taken to move away from GSuite to Office 365 and the Exchange/Outlook combination.
I've found things that were so simple in GMail to be absolute torture in Outlook - searching from all email from a domain now involves the use of complicated search folders instead of typing "from:example.com" in the search bar; delay-sending email is hidden in hierarchies of menus and now spam is handled by a third party rather than just dropping into the "spam" folder for you to decide what to do with it.
Email Encryption - A Crappy(ta) Solution
Another run in with the local council and the guys at Capita who manage the council tax left me amused. Everytime I contact the council tax guys by email, they insist on responding with some sort of email encryption system.
I'm entirely for email encryption. It's true that the security of email in transit cannot be guaranteed, so any point-to point encryption is an improvement on a pretty flawed system. My preference is for proper encryption such as PGP, but the system employed by Capita positively amuses me - it's all done online on a HTTPS wesbite, but fails to deal with the salient security points. This is my basic analysis: