Question Outlook 2k19 - randomly doesn't save sent items in sent items

[Kanc1erz]

Hello,
I have an issue that outlook doesn't save sent mails in proper (any) folder. It's rather uncomfortable as I don't have any proof that I sent the mail
After reading the Internet and going through settings I noticed one thing - when I am replying or creating new message and when I click options -> save sent element in... there is SOMETIMES don't save "ticked". What does sometimes means? Almost 50% of new outlook session has checked don't save and other 50% - use default folder. Moreover - when don't save is chosen and I check use default folder (or any other) I need to do it everytime as the previously ticked option doesn't stay there....
I would like to rather not reinstall whole Office. Repair (whole office) of course didn't help at all in this matter. Inbox repair also hasn't changed anything.
Does anyone has some ideas how to force Outlook save sent items in default folder (or any other, it doesn't matter)?

 

[Ralston18]

Not sure where you are looking and I do not see a "sometimes"....

Outlook Options > Mail > Change the settings for messages you create and receive > Scroll down to Save messages.

Are all boxes checked? What time is Automatic Save set at?

Check all other settings as well to ensure that they are set as you expect or need them to be.

If/When you make changes be sure to "OK" those changes to make them permanent.

 

[Kanc1erz]

Hi, under save messegaes checked is first option (3mins), fourth and fifth. Of course it was checked at the very beginning.