Lost services after every Microsoft up date

Regarding Outlook:

In Outlook, go to File > Account Settings > Repair to rebuild the mailbox connection.

Open Control Panel

Search Mail

Click Show Profiles

See if there is more than one profile

Select your old profile and click Set as Default

Regarding Printer:

Press Windows + R

Type services.msc

Find Print Spooler

Right-click → Restart

Uninstall > Reinstall Printer driver.

Settings > Update & Security > Troubleshoot (or Settings > System > Troubleshoot

Select "Printer" and run the troubleshooter

Is this happening in new Outlook or classic Outlook?

What type of email account do you have configured in Outlook? POP, IMAP, Outlook.com, or Microsoft Exchange? You should not lose anything with Microsoft Exchange accounts or POP accounts in classic Outlook.

Mailboxes in new Outlook are stored in the Microsoft cloud and you shouldn't lose content unless you delete the account from Outlook and the cloud.

If classic and you are using imap account, the contacts are in folders named “(This computer only)". It sounds like the data file is getting removed and Outlook has to make a new one. Do you have a c:\windows.old folder after updates?