You can, but only if they let you.
It is extremely important that a person's fiduciaries (executor, trustee, or attorney-in-fact under a power of attorney) have access to your digital information - photos, emails, bank accounts, financially valuable websites, blogs, Twitter accounts, etc, etc, etc.
Under the federal "Secure Communication Act" service providers (like Gmail, Facebook, banks) cannot (ie, are forbidden to) provide account content to anyone, unless one of the act's exceptions apply.
The SCA focusses on privacy, and prohibits anyone from accessing a person's accounts. It may seen obvious that a fiduciary would inherently have authority to access her principal's on-line data. It's not. Service providers are wary of violating the law, and so are treading lightly.
Exception #1 - "lawful assent". In Ajemian v. Yahoo! the Massachusetts SJC has recognized an executor's inherent authority to "lawfully consent" to an executor's inherent authority to "lawfully consent." This is a great start, but disclosure, recall, remains voluntary under the SCA.
Exception #2 - acting as "agent" of the principal. The Ajemian court also held that an executor is not the decedent's agent, since the source of the executor's authority is the Court, not the decedent. I do not agree, but for now, at least, this is the law, at least for Massachusetts purposes.
This is good news, but is only step one; even with lawful consent, service-providers are not required to provide account content - compliance is totally voluntary!
By the way, the Ajemian court also placed a welcome cloud over the enforcement of a service provider's "end user license agreement" (EULA) which also may prohibit disclosure (regardless of the law), as a matter of agreement between the user and the service provider. I say welcome since, as we all know, one cannot sign up for an on-line account unless she "agrees" to the EULA. In my mind, EULA's are "contracts of adhesion" and unenforceable against the user. Stay tuned.
So where are we now?
>> Massachusetts has spoken, but that does not mean its decision is the law in any other state.
>> If the "agency" exception requires the account owner to authorize the fiduciary as an agent, then the account owner should sign a document to that effect.
>> Even if an executor can grant lawful assent, that does not mean that a trustee can. Wills, trusts, and powers of attorney should include specific digital authorization.
>> Disclosure remains voluntary. Not sure how to deal with this one!
>> Keep an updated list of usernames and passwords, and arrange for your fiduciaries have access when and if needed.
>> Hope the EULAs are ultimately determined to be unenforceable against an account owner and the owners fiduciaries.
>> Make local back-ups of all data!
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