Sending encrypted attachments with Apple Mail

Question

Ocean 17 Author

Level 2

202 points

Sending encrypted attachments with Apple Mail

I have to send a W9 to a corporation because I'm going to be a contractor.

They really told me to just attach a pdf to an email, and send it.

I feel totally uncomfortable sending my social security number that way.

I searched for ways to encrypt email, and came across sendinc: https://www.sendinc.com/

This way, the email gets decrypted only at the receiving end, and if it is read by someone else, he can only see the encrypted content.

What's your experience sending tax documents and sensitive information through email?

MacBook Pro with Retina display, OS X Mavericks (10.9.4), 512 Gb SSD, 16 Gb RAM,

Posted on Oct 2, 2014 4:04 PM

Reply

Answer 1

Old Toad

Level 10

215,706 points

Oct 2, 2014 4:24 PM in response to Ocean 17

When you do a Save As (hold down the Option key) on the pdf file you can give it a password required to open and print it. You can then call the company and give them the password verbally.

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Answer 2

Ocean 17 Author

Level 2

202 points

Oct 2, 2014 5:13 PM in response to Old Toad

Thanks, Old Toad, but this wouldn't encrypt the pdf, just password-protect it?

I researched, and found that password protection of pdf documents is easily circumvented. There is free software to do that.

For my case, I used sendinc to send the document encrypted.

It's incredible how many people send pdf forms of tax documents with their social sec nr unprotected and open through email. That's asking for ID theft.

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Answer 3

Barney-15E

Level 10

122,246 points

Oct 2, 2014 6:35 PM in response to Ocean 17

You would need a cross-platform solution that the company also uses. When you send them an encrypted file, they will just trash it and your application.

Take a hard copy opy into them directly If you are concerned.

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Answer 4

Barney-15E

Level 10

122,246 points

Oct 2, 2014 7:32 PM in response to Ocean 17

It would be something the company has to deal with. It is not using something they are familiar with. Instead of the requested document you are going to send them a link to something they know nothing about. And, they have to create an account to access your email.

Depending on the company’s email policies, the links could be stripped off the email.

Contact the person you are sending the file to and ask them if they can deal with that. Otherwise, you’re just taking your chances.

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Answer 5

Ocean 17 Author

Level 2

202 points

Oct 2, 2014 6:59 PM in response to Barney-15E

Thanks, Barney, but I thought sendinc would be cross-platform, and decrypt the message to the sender.

Otherwise, what use would sendinc be of, otherwise?

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