Workflow for sharing sensitive PDFs with non-tech savvy folks?

Hi all,

I’m helping a member of our extended family close out an estate in the coming months and will be sending lots of forms back and forth between legal folks and financial institutions with sensitive data on it (social security numbers, etc.)

Trying to find a good balance between keeping data somewhat secure in transit (mostly email) but also easily viewed by a receiving party that likely won’t be very tech savvy.

In the past, I’ve handled this balance by placing PDFs with sensitive info into DropBox folder and just shared the link via email with the relevant party – and then use a Hazel rule that goes in and automatically deletes the DropBox file after 7 days so the link vanishes.

I’ve also done password protected PDFs before, but have found that to often be more trouble than it’s worth since inevitably the document needs to be read by someone else in the agency/institution and the password doesn’t get to them, causing frustration for everyone.

Just curious if anybody has a cool workflow for this or a service they trust (something like OneTimeSecret does for passwords). Realizing as I write that I could probably put DropBox link in OneTimeSecret also/instead.

Wondering how other folks handle stuff like this. Thanks in advance for suggestions!


I’ve heard good things about DocSend


I would not email documents of any kind if there is any risk that the email could inadvertently be forward to the wrong person.

You could use the Share / Collaboration feature in iCloud:

CleanShot 2023-06-24 at 17.13.40@2x

Use iCloud to share and collaborate on files and folders – Apple Support (UK).


1 Like EE2E and free tier has full sharing features.

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Put it in an encrypted ZIP or (if both Parties use Mac) DMG image.

Ahhhh, wasn’t aware of this. Could be perfect – thanks a ton, Wayne. :pray:

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But this would require other party to be using iCloud as well, yes?

No, it does not require the other person to be using iCloud in my experience. There are a variety of settings to control whether you’re sharing it as read-only or editable, whether they can share it with others, etc.

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Ahhh, cool. I’ll check it out – thx a ton! :pray: