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Every time there is an update to your operating system, there is a risk that applications currently installed will have a failure due to a change in shared library code on which they depend. I see unstable behavior on my Windows machines when the corporate IT staff have pushed updates that partially install while other parts "need a reboot" to complete. Patches are usually issued as a "suite" of tested items that need to be applied as a set. On Android, it is typical to see re-issues of applications after an OS patch. Ditto on IOS platforms e.g. iPad where a system update necessitates fixes to applications to work correctly.

On the topic of passwords: find a password manager e.g. KeePass or Dashlane that secure the passwords by application. I have to maintain a large number of passwords that must be unusually complex to meet the imposed standards. KeePass keeps them encrypted in a local file that can be backed up to a thumb drive. Dashlane is cloud oriented and maintains an encrypted copy.

The encrypted passwords in my environment are on top of session encryption using PKI, CAC and other related technologies. Browsers tend to keep password information in cookie files and those get wiped on a cache clear and sometimes as part of a browser update that changes how the cookies are stored and retrieved. You need to more robust solution. KeePass is a pretty simple option.