I’ve also just encountered an issue in which some link sequestering protections deployed in our Exchange environment end up consuming a one-time use of a link (e.g., a Salesforce password reset email came with the URL wrappered and thereby already expired; some phishing testing we were doing in house showed almost all trial emails “clicked” within the same minute they were sent—actually triggered by the same URL wrapper)
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Just a suggestion- buy a small solid state usb disc- put all your pdf files and password data on it and a password to open it send it to her. call her or separately mail her the password for the thumb sized disc. consider buying two or three such and use for backups or copies.
I have three methods:
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For individual documents to family members, iMessage.
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Sometimes an encrypted PDF in eg Dropbox when we’ve previously agreed on a password (in discussion over FaceTime).
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For sharing files with ‘strangers’, I use 1Password’s secure sharing feature. Since you can add documents, arbitrary fields, and notes to 1Password items you can basically share anything. In the past I’ve even created a ‘note’ item and used it to write out (markdown-formatted) instructions/info and attached a file to the note. It’s a nice attractive way to provide a secure document to non-techy people. The secure sharing allows options such as limiting the recipient to a specific email address and time- and view-based limits.
iMessage when I can.
Encrypted file to Google drive (password on paper) when I have to. At least there I can enforce that only a certain user gets access to the file regardless of what happens with the link to that file.
Paper instructions and master passwords in sealed envelope in a safe at home. My brother and brother in law have access to that should both my wife and I become incapacitated.
Similar for me…there’s a 911 vault in my 1PW online account that has a sufficient number of things in it that our son can be us once he gets physical access to at least one of our devices and he’s got paper in his safe with the same info. He’s got a key to the 900 mile away house and the garage code as well.
I very much appreciate the replies w/suggestions for my situation; it brought forward options I had not considered, for which I’m extremely grateful.
But please understand that my initial post was to show support for Adam’s idea of an article re:sharing sensitive info over the internet; I mentioned my dilemma merely as one example as to why I would find such an article helpful.
A thousand thanks for all the great ideas. 
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(late to the thread)
I’ve used https://onetimesecret.com/ to send passwords in a second channel.
One time secret only allows the secret to be accessed once and then the enclosed secret is destroyed. You can safely pass the secret as well as detect that the secret may have been compromised.
Does this also prevent sending an SMS message to an Adroid phone?
No. If the number isn’t registered to iMessage, it doesn’t receive iMessage, and you continue to use SMS. It only disables fallback if the number is using iMessage and is registered to it, and even when you’re offline.
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