I need to send a large file securely (too big for my e-mail)

I’m in a pickle. I need to send a large 53 Meg file to my insurance company, but my e-mail will only allow me to send something that is 25 Meg in size. And the company only provides me with a fax number or yet another e-mail address to send this to. They don’t have an FTP apparently. Is there a way I can do this, or a safe, secure 3rd party source? It has my medical stuff in it, so it needs to be really secure.


Most medical offices have some sort of online record system where you can transfer files. These guys don’t have one of those? If not, that’s pretty terrible.

Aside from that, the first thing that comes to mind for me is dropbox. You can upload the file to your dropbox and share a link to it and they can click to download the file.

There are also secure file transfer services that will perform the same service for you. I don’t use one, but I’ll bet you dollars to donuts that by tomorrow morning you will get five people posting services they use to do that.

REALLY secure is iffy but Dropbox, Google Drive, and OneDrive could all handle this.

At work, we use WeTransfer.

It’s the insurance company. You know… trying to make it impossible to keep my small disability pay.

Zip it up encrypted with a password, put it on your cloud drive of choice, then share it to them. Delete when they confirm they have it.

Having a file in their email inbox is probably less secure than sending them a link to a Google Drive hosted file, where you set the file to allow access to only invited users. And then yeah, add a zip password. I think Windows file unzip does support passwords on zip files, at least for opening, so probably whoever is receiving the file can figure out how to unzip it if you add a password to the file itself.

If you’ve got an Apple device you can use Mail Drop. It supports files up to 5GB.

I agree with password protecting the ZIP file if it’s going to their email. Give them the password in a phone call.

Oh yes very important point, don’t email the password.

What I have done for the password is share a separate Google Doc with just the password in it, no other information, then after they read that document and use it to open the zip, delete it and remove it from trash, so there’s nothing in the email after that point that can decrypt it.

Was just coming to say WeTransfer, but Gladguy beat me to it.

WeTransfer-fan here as well, I use it all the time for large files. But to be honest, the files I share are not confidential or personal, so I have never felt the need to look into the security of WeTransfer…

WeTransfer is fairly secure; one of the largest marketing firms on the planet has it as an approved transfer service for files containing PII with entities outside their company, I can say from firsthand experience.

It is exponentially more secure than simply sending personal, confidential files via straight email in a zip file as Jeff was originally looking to do, that’s for sure.