Answering my own question, I did an experiment and tried adding a new user 
(while working) and upgrading and could still log in. Based on that, I 
updated my user password while working and upgraded, and it worked. So 
maybe something about how the old passwords were stored/encrypted.

Anyways, that got me over the hump at least.

On Tuesday, March 9, 2021 at 1:28:27 PM UTC-6 [email protected] wrote:

> I asked about this a couple months ago but did not have time to really dig 
> into it then.
>
> I am currently on Jenkins version 2.265 with the latest version of all 
> plugins (that I can update). When I upgrade to 2.266+ (have tried with 
> latest), the server restarts but my user login no longer works ("Invalid 
> username or password"). If I manually roll back to 2.265, everything works 
> again. I assume this is related to 
> https://github.com/jenkinsci/jep/tree/master/jep/227.
>
> * No warnings or errors in the logs on server startup or when login fails
> * The server is up and working normally afaict (public viewable stuff 
> works, it's detecting scm changes, doing builds, etc)
> * Using: Jenkin's own user database
> * Using: Project-based Matrix Authorization Strategy 
> * Plugins: I have some plugins installed of course but it's hard for me to 
> imagine what plugin could be affecting logging in. I've looked at the 
> plugin compatibility list for 227 (
> https://github.com/jenkinsci/jep/blob/master/jep/227/compatibility.adoc) 
> and compared to my plugins but unclear what could be the issue. I use 
> Credentials and Matrix Authorization Strategy plugins but those are marked 
> as compatible. Some plugins I have installed but with unknown compatibility 
> that might possibly be related:
>   * Authentication Tokens API Plugin (don't think I'm actually using this)
>   * Cloudbees AWS Credentials Plugin
>   * Credentials Binding Plugin
>   * SSH Credentials Plugin
>
> How do I fix or debug this? It's easy to flip between working and broken 
> states by just swapping wars but I'm not sure how to tell what's not 
> working or how to fix it.
>
> Thanks!
>

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