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Not sure if this is the right place to ask, but here goes:

My spouse and I have 20-ish or so accounts (retirement, investment, banks, insurances, tax, etc.) where I would we both would like to have full access. Should something happen to one of us, the other needs to be able to access all the key resources and be able to conduct business as needed (without some major legal wrangling).

Many of these accounts these days have two factor authorization, secret questions (which are often silly and unanswerable), and/or rotating passwords with different set of password rules. They often don't offer an option for joint account ownership.

We used to just share account link, user name and password (encrypted). But that doesn't work anymore, because two-factor authentication and frequent password updates.

How do we do this in a way that's reasonably easy and safe?

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    Most, if not all of these services should understand that the accounts belong to two people and give each of you access under a separate identity. This works best because then your spouse represents theirself instead of impersonating you to manage accounts. Banks and insurance companies especially should allow multiple logins for your account for the same reason. – nbering Apr 21 '18 at 23:20
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    If a service provider doesn’t allow multiple logins, ask them to consider it. Many may have never considered it, and it may not be that difficult to implement. – nbering Apr 21 '18 at 23:24
  • What form of OTP are they using, TOTP would be easy to backup, whereas text messages or U2F would not – jrtapsell Apr 22 '18 at 0:07
  • @nbering: they should but they don't. Some don't offer joint accounts, some require you to close and open new accounts. – Hilmar Apr 22 '18 at 13:03
  • @jrtapsell: sorry, I have no idea what any of these acronyms mean – Hilmar Apr 22 '18 at 13:04
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  • Share name and password as usual
  • Secret questions are stupid, just treat them as another password (put randomly generated text there and shere it)
  • rotating passwords: If you don't mind the reduction in security, just share the rules the same way you share passwords. If you do, there is not an easy way to do this.

2FA

  • TOTP, you should add it to both of your phones when registering. If that is not feasable, consider using a TOTP app that allows backups and share the backups. You could also share the QR code/secret in text form, but that reduces security somewhat.
  • U2F unless the site allows two tokens for your account, than this may be impossible to share. Maybe there is a token with a backup feature, I don't know.
  • SMS: This one is also a bit tricky. You may want to set up some sort of SMS cloud backup and give your spouse access to that, or make it possible for her to get a new SIM for your number.

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