Are Gmail emails sent through Outlook encrypted?

[jmt356]

In my Outlook Internet E-mail Settings, I have “This server requires an encrypted connection (SSL)” checked. Does this mean that emails I send through Outlook are encrypted? If I am sending a Gmail email over a public network (e.g., a hotel) or a private network where someone else has the Wifi password (e.g., at someone else’s home), can Gmail emails sent through Outlook be intercepted and read?

[StuartR]

SSL encryption ONLY covers the communication from GMail to Outlook. Once the emails arrive at the GMail server they will be unencrypted. This includes their full journey from GMail to the recipient. I have come across incidents where someone was able to tap into public network connections and read all the emails being sent and received.

[jmt356]

Is there anything I can do to prevent the unauthorized viewing of my Gmail emails that travel between Gmail's server and the recipient? Is abandoning Gmail the only way to avoid this?

[HansV]

Hmm... Gmail uses https - doesn't that mean that communication with Gmail is encrypted?

[StuartR]

Hmm... Gmail uses https - doesn't that mean that communication with Gmail is encrypted?

https: encrypts traffic between the users browser and the Gmail server.
The Gmail server then sends the email to the destination server in plain text using SMTP protocol.
It is possible that the destination server may encrypt the email on the final leg of its journey to the end user.

[JoeP]

If the OP is concerned with only the email content he could construct the body of the email in a separate document, save it, encrypt the saved file, and attach it to an email. 

Also, see Encrypt email messages

[Jay Freedman]

If the OP is concerned with only the email content he could construct the body of the email in a separate document, save it, encrypt the saved file, and attach it to an email. 

If the sender and recipient both use 7Zip, it supports AES 256-bit encryption of compressed files. With a password of 16 to 18 characters, the encryption would be unbreakable for practical purposes.

[StuartR]

Another good solution for encrypted email is PGP. This page describes a number of tools for integrating PGP with your email. As with most encryption solutions, the most challenging parts are key management, and ensuring that the person you are communicating with has compatible capability so that they can actually decrypt your messages.

[jmt356]

My main concern is in using Outlook as an email client. I have heard of some people/companies that have abandoned Outlook because of security concerns. However, based on the above posts, it seems that the main vulnerability with respect to using Gmail on Outlook is that emails can be intercepted and read when being transmitted between Gmail's servers and recipients' servers. It appears to me that this risk would remain whether I continued to use Outlook as my email client or used gmail directly (e.g., through IE or Chrome).

Are there any additional risks in using Outlook to access my email on public Wifi networks that I should be aware of?

[StuartR]

If you are on Public WiFi then there's a whole load of additional risks. Chief, among these is that the WiFi router can redirect all your traffic to fake servers which can do whatever they like. I recommend always using a VPN when you do anything at all on public WiFi.

[jmt356]

What are the chances that the public wifi at a reputable establishment such as an airport or a Starbucks café would redirect traffic to fake servers?

[StuartR]

What are the chances that the public wifi at a reputable establishment such as an airport or a Starbucks café would redirect traffic to fake servers?

Much higher than you might expect. Anyone can sit at a table with a laptop and offer a fake service that looks like the real thing.

[jmt356]

I still don't understand.

Suppose I send an email from Gmail.com on Chrome to another email account on Gmail.com on Chrome. Is the message encrypted and immune from being intercepted and read?

What if I send an email from my Gmail account on Outlook to another user’s Gmail account on Outlook. Is the following true:
- On the journey from Outlook to the Gmail server, the message is unencrypted and can thus be intercepted and read;
- On the journey from the Gmail server to the recipient’s Outlook client, the message is unencrypted and can thus be intercepted and read.

According to https://gizmodo.com/every-single-gmail- ... 1548130115" onclick="window.open(this.href);return false;, "Google just announced that Gmail will be all encrypted all the time. More specifically, every single email you send or receive will use an encrypted HTTPS connection, regardless of which device you're using and which network. Even public Wi-Fi is okay."

This seems to imply that even if I am using Outlook as my email client and even if I am on a public Wi-If connection, my messages will still be encrypted and impossible to read by unauthorized third parties. But this appears to be inconsistent with posts 201450 and 201650 above, which imply continued vulnerabilities with Gmail.

[HansV]

Chrome > Chrome: sender and recipient automatically use an encrypted connection.

Outlook > Gmail > Outlook: you as sender can specify encryption for outgoing messages in Account Settings > Change > More Settings > Advanced tab.
The recipient can do the same for incoming messages, but you have no control over that.

[DaveA]

I see a hole in this. When sending any email from any program, it must get from your computer to the Gmail server. So at this time there is no encryption, but from Gmail server to server there is.

Now if one was to be logged into the Gmail through a browser, then it well be encrypted, from the start, because it is already at the Gmail server.

When and where is the Gmail decrypted?

[HansV]

When sending any email from any program, it must get from your computer to the Gmail server. So at this time there is no encryption

You can specify that Outlook uses encryption to send email:

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[DaveA]

OK, thanks