Going Paperless...security question

I am really trying to start going paperless, I bought @MacSparky paperless guide a few weeks ago and while I have been trying on and off for some time to go paperless, I have decided to go all in!

Do you guys that are paperless have everything including personal documents like wills, life insurance docs, social security cards etc. I am going to be using Evernote.

I have scanned all my documents, but the more important (wills, life insurance docs, social security cards …) i keep in paper. But even then i got rid of 5kg of paper. I keep them just in folders, because i don’t want to depend on other apps.


Most of my paperless files go to Dropbox, but for particularly sensitive documents (tax returns, for instance) go into a folder on my iMac that does not get synced to a cloud service (though it does get backed up offsite via Backblaze).

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I use Dropbox for my paperless storage. However for private documents like financial and identity documents, I use an encrypted sparse bundle disk image that is stored on Dropbox (but encrypted locally so a rogue Dropbox employee or hacker cannot easily access).


I do scan all my critical personal documents in and strore them on my system but wills, estate planning, trust etc have to be originals to be valid so the real ones are kept in a fireproof safe. The electronic copies are to provide initial info for the people who would need them but they can’t be used as legal documents.


Just scan it as a PDF and then use Automator to encrypt it. https://macosxautomation.com/automator/encryptPDFs/index.html

Use a password that is longer than 30 characters and store it in your password manager and you’ll be fine.


Good suggestions above.

Once you decide on filing practices, backup strategy, etc., don’t forget to document all of this for others in case you are incapacitated or dead. You should create paper documents with passwords, access instructions, and a description of your computer file structure. Don’t forget your computer screen access password, your master 1Password or LastPass password, PINs, email passwords, etc. Just think about how someone would access your digital life if you can’t.

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I went paperless a long time ago, I scan and destroy everything.

I keep all of my documents in a google S3 bucket so that I can access them more programmatically then Dropbox/Drive/iCloud. And I can use my own encryption key.

I would echo what @Arthur said, make sure that there is a limited back door into the system, in the event of your death. I know that google can be auto configured to give access to files in the event that you have not logged in, in three months or something.

I usually scan everything but keep paper copies of anything that requires an original paper copy like wills, power of attorney, marriage & birth certificates, etc.

While I have the registration and insurance cards in my cars, I have an electronic copy on my iPhone and iPad. I also keep stuff in 1Password like insurance cards, credit cards, passports, drivers licenses.

If you go all in on paperless make sure you have a very good backup and disaster recovery plan in place. Testing your backup and recovery is also important.

I scan, then shred everything. All documents even sensitive docs go to Dropbox but I encrypt prior to upload with AESCrypt, and that’s a program that works for both Mac and Windows and iOS so you don’t get caught out when it comes time to decrypt.

I always look at whether if something happened to me, someone taking care of my affairs afterwards would absolutely need the hardcopy. That’s what I keep in a safe at my bank. everything else is scanned and shredded.

At this point, many states still require original paper copies of wills. I shudder at the thought of someone’s shredding a will still considered to be in effect.

JKoopmans - My opinion: it is probably NOT a good idea to keep a will in a bank safety-deposit box. After a bank is notified of a death, a court order will probably be required to open the decedent’s box. Keep in mind that a Power of Attorney ends when a person dies, so even a POA agent cannot open the bank safety deposit box w/o a court order assigning an executor/administrator. A better plan would be to store the original will in a home safe or in a legal office, notifying appropriate family members and beneficiaries of the location.

In many cases, a trust document might be superior to a simple will. This does away with the complications and delays of dealing with court supervision. The same considerations for digital vs. physical document storage apply, with the exception that a Trustee, without a court order, should be able to access a bank account and a safety deposit box titled in the name of a trust. Even in that case, the Trustee will need the original paper version of the trust, so it shouldn’t be stored in the bank safety deposit box.

All of the measures we take to digitize, store and back up documents are for nought if our incapacity agents, heirs and beneficiaries cannot access the required paper documents and digitally-stored documents.

Edited to add: In the last few months I have dealt with the death of two family members. Take my word for it - banks will immediately shut down all access to bank accounts, credit card accounts and safety-deposit boxes upon the death of the account owner, if this is an individual account.

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I take this moment to remind our forum friends, that on the internet people are from everywhere! And that different countries have different laws.

If you have concerns check with a local lawyer about this stuff rather then what people say on the internet, though that stuff about the bank seemed useful.

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@Arthur as @Ben_Lincoln said.

As I live in the Netherlands the issue you describe is not actually an issue for me. All our wills are centrally registered and can be accessed by the notary that handles the estate. The copy I have at home is just that: the copy.

Any bankaccounts, safes etc will be handed over to my beneficiaries, or the executor of my estate, within a few days of the Notary starting procedings, which usually takes little time.

So I’m not worried about that. For me, the safe is safe (pun intended)

I scan and shred almost everything. I put everything in Dropbox. I confess I’m not overly worried about the data stored in there - everything goes into it, including tax returns and medical records. I could walk out of the burning house tomorrow and have everything we need to get going as soon as I get internet access.

I do keep important papers - birth certificates, wedding certificate etc - in hard copy with scanned copies on Dropbox. But it’s less than half a filing cabinet draw in total.

I wouldn’t store anything unencrypted on any cloud service.

I use DEVONthink which transmits and stores the data using AES 256 bit encryption on iCloud drive. You can use Dropbox, etc, too.

I consider Evernote, with 2FA, to be as secure as any online storage, especially now that the files reside on Google. And the bulk of my personal files are in EN. However, I never store any document in Evernote, or any online file/folder storage, that contains my social security number unless it is encrypted. In the past, I pre-encrypted this type of file before upload. Today, because I am almost 100% mobile, I store them in 1Password.com.


Yes, that’s very important to consider. While I might say that my social security number is a worthless piece of information, since there’s absolutely nothing you could do with it, US citizens should treat it as very sensitive information.

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Does DEVONthink automatically encrypt all files stored or is there a setting that has to be enabled? I was thinking of doing exactly the same as you Jeff DEVONthink Pro Office (which I already have stored on iCloud Drive. Does it work and sync well?