Fail to upgrade synapse from 1.59 to 1.69

It sounds related to the fact that you probably increased the password policy to enforce lower/uppercase chars etc, but probably the mechanism that generates a random password for that special synapse user doesnt generate such a password (but it is a 30-char long password tho) …

One workaround can be to temporarily reset the password policy while upgrading/install/restoring the app I suppose

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