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Windows 7: how to encrypt email? easy/best way?

22 May 2013   #1

Win 7 Pro, Mac OS Sierra
how to encrypt email? easy/best way?

I know their are web based solutions for sending encrypted emails or Online Encrypt/Decrypt your text messages - ??? (never tried them do they even work? beats me)

I think it gets more confusing and difficult to setup and use if you try configuring computers and email clients to do this?

so, what is the best way to send and receive encrypted emails? is it even possible?


My System SpecsSystem Spec
23 May 2013   #2

Windows 7 Home Premium x32 SP1


it is possible. Depends on where you would like to encrypt them: locally or on the web servers.
Have you heard about PGP/GPG before?

GPG is an open source free version of PGP.
The GNU Privacy Guard -

Wikipedia info:
It's available for almost all platform, if you have Windows OS worth to try is GPG4Win.

In short PGP/GPG uses symmetric key cryptography.
First you have to create your own key (public and private key).
Your public key is for people who will email with you - they have to know what your public key is, because they will use it to encrypt message for you.
If you want to send encrypted message to other person then you will need their public key and your private (secret key).

It sounds complicated but in practice it isn't.
Here are some tutorial vids you will be helpful I hope:
GnuGPTutorial - YouTube

Above example is how to encrypt your email/files locally, but there are also webmails which offers this feature - they do all this work on web servers like: Countermail or HushMail - however I don't know how much they are reliable and secure since everything is hidden for end user.

I'd recommend to use PGP/GPG encryption on your own computer if you have time to learn it. It's easy in fact but needs few minutes to understand how it works.
Setting up GPG, and learning it, would be next...but you will never get all your contacts to use it. Unfortunately.

My System SpecsSystem Spec
23 May 2013   #3

Win 7 Pro, Mac OS Sierra

tried PGP once years ago, it was complicated, never did get it to work. and of course like you said, if the person im sending the email to don't use it, then thats a problem too.

those videos help so I will check those out. thanks.
My System SpecsSystem Spec

23 May 2013   #4

Win7 H.Prem. 32bit+SP1

Hi macgig,

I think this is, at first glance rather complicated but it can work.
Send an email to everyone you want to send encrypted messages to, stating they will get messages as an attachment that was written using notepad or wordpad. The files will be compressed and password protected using 7Zip, then send your password i.e. your phone number without the area code.
My System SpecsSystem Spec
23 May 2013   #5

Windows 7 Home Premium x32 SP1

macgig you are welcome.

Roderunner, yes but as you mentioned password should be send via safe channel.
How to determine safe channel? What is secure and what isn't in certain circumstances - that's hard to tell.
Also password should be changed everytime you send message.
With PGP there is TFA (two factor auth.) - your secret (private key) which is unique and password to your private key.
Key without pass means nothing and password without the private key is useless.
Plus you don't have to send any password to other person - she/he only need your _public_ key which can be send via unsecure channel.
My System SpecsSystem Spec
23 May 2013   #6

Win 7 Pro, Mac OS Sierra

even with encryption, I have to wonder if an email is still secure? if it's not 100% secure 100% of the time, then Id have to ask what is the point and why even bother to encrypt it in the first place?

I wanted to set up the GPG program and test it. I made two test email accounts, and trying to get them to work via outlook 2003... which keeps crashing... so far my experiment is a big pain.. not easy. guess I need to forget outlook and try another email program.

only reason I'm trying is I have a client that asked me how to encrypt email. I have no idea but figured i'd try to learn. lol
My System SpecsSystem Spec

 how to encrypt email? easy/best way?

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