Gmail showing authentication info

Yesterday Gmail announced on their blog they would be pushing out some new UI to users to show the authentication and encryption status of email. They are trying to make email safer.
There are a number of blog posts on WttW for background and more information.

The short version is that TLS is encryption of the email between the sending server and the receiving server.  It means mail can’t be intercepted or changed while between one server and another.
Gmail is now showing users whether a mail was sent using TLS.
If a message is sent without using TLS, there is an open red lock shown.
Open red lock = unencrypted
If you hover over the open red lock, Gmail tells you the “message was not encrypted”
Hover showing "message not encrypted"
Using TLS removes the open red lock.
Mail sent over TLS
These messages went to spam because, well, do you know how hard it is to find a mail server that’s not authenticated? I ended up sending using SWAKS from one of our VMs so I could control a whole bunch of things, including whether or not mail used TLS. Interestingly enough, Gmail was happy to accept the mail over IPv6 but temp failed anything I sent over IPv4.
Gmail is, apparently, also notifying if mail being sent is going to a recipient on a server not using TLS. I don’t have an easy way to test that.

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Google Postmaster Tools

Earlier this month Google announced a new set of tools for senders at their Postmaster Tools site. To get into the site you need to login to Google, but they also have a handy support page that doesn’t require a login for folks who want to see what the page is about.
We did register, but don’t send enough mail to get any data back from Google. However, the nice folks at SendGrid were kind enough to share their experiences with me and show me what the site looked like with real data, when I spoke at their recent customer meeting.
Who can register?
Anyone can register for Google Postmaster tools. All you need is the domain authenticated by DKIM (the d= value) or by SPF (the Return Path value).
Who can see data?
Google is only sharing data with trusted domains and only if a minimum volume is sent from those domains. They don’t describe what a trusted domain is, but I expect the criteria include a domain with some history (no brand new domains) and a reasonable track record (some or all of the mail is good).
For ESPs who want to monitor all the mail they send, every mail needs to be signed with a common d= domain. Individual customers that want their own d= can do so. These customers can register for their own access to just their mail.
ESPs that want to do this need to sign with the common key first, and then with the customer’s more selective key.
How does it work?
Google collects data from DKIM and/or SPF authenticated mail, aggregates it and presents it to a Google user that has authenticated the domain.
How do I authenticate?

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Lets Encrypt Everything

Using SSL TLS to protect data in transit and authenticate servers you contacted originally required specialized software, complex configuration and expensive and complicated to require certificates.
The need for specialized software is long since gone. Pretty much every web server and mail server will support SSL out of the box.
Basic server configuration is now pretty simple – give the server a couple of files, one containing the TLS certificate and the other the associated private key. (Configuring a server securely, avoiding a variety of attacks on weak parts of the SSL/TLS protocol, can be a bit more work, but there are a lot of tools and documentation to help with that).
But acquiring a certificate from a reputable provider is still expensive enough (one Certificate Authority’s list price for entry level certificates is $77/year, though the same certificates are available for <$10/year from resellers, which tells you a lot about the SSL certificate market) that you might not want to buy one for every endpoint.
And the process of buying an SSL certificate is horrible.
First you have to find a Certificate Authority or, more likely, a cheap reseller. Then it requires generating a “Certificate Signing Request” – something that can be done in dozens of different ways, depending on the device it’s being generated for. The user-friendliest way I’ve found to do it is to use the openssl commandline tools – and that’s really, really not very friendly.
Then you need to log in to the CA, upload the CSR, follow a bunch of directions to confirm that you are who you say you are and you’re entitled to a certificate for the domain you’re asking for. That can be as simple uploading a file to a webserver that serves the domain you’re getting a certificate for. Or it can turn into an inquisition, where the CA requires your home address and personal phone number before they’ll even talk to you.
Then you need to use the same browser you submitted the CSR request from to get your certificate – as the CA doesn’t do all the cryptography itself, it relies on your web browser for some of it. There are some security-related reasons why they chose to do that, but it makes for a fragile – and near impossible to automate – process. And the attempts to upsell you to worthless “security” products are never-ending.
help
There’s probably more horribleness, but it’s 9 months since I last bought a certificate and I may have forced myself to forget some of the horror.
There’s no need for it to be that painful. It’s easy to mechanically prove to a Certificate Authority that you control a domain in the same way you prove ownership to other companies – put a file the CA gives you onto the webserver, or add a special CNAME to your DNS.
And once you’ve proved you own a domain a certificate for that domain could be generated completely automatically. For the most common web setups you could even prove domain ownership, generate a new certificate and install that certificate into the webserver entirely automatically.
I’m sure there’s some reason other than “because we’re milking the SSL cash cow for all it’s worth” that dealing with most Certificate Authorities is so painful and expensive. But there’s no need for them to be that way.
This year there’ve been several groups who have stepped forward to escape the pain of dealing with legacy Certificate Authorities, at least for basic domain verified TLS certificates (as opposed to the “green bar” extended verification certificates you might want for, e.g. an eCommerce site).
Lets Encrypt has been one of the higher profile new CAs who are driving this effort. With the help of ACME, an open protocol being developed for issuing certificates automatically, they’re providing zero-cost TLS certificates. They’re hoping that, to use their phrase, you’ll encrypt everything, using TLS to encrypt traffic everywhere it makes sense to do so.
So, how does it work?
coyote
It works wonderfully well.
Lets Encrypt is still in public beta testing for a few more weeks, but I just got beta access. Installing their client tool on a reasonably recent Linux box just took copy-pasting two commands and waiting a minute.
The tool supports a variety of different ways to request a certificate – from entirely automated for a vanilla Apache installation through to the most complicated, entirely manual.
To see how difficult it was I decided to install a certificate for blighty.com, a domain on one of our very old webservers – one that was too old to install the letsencrypt tool itself. Fully manual! For a website on a different server!
I ran the letsencrypt tool, telling it I wanted a certificate for blighty.com. It gave me a the contents and location of a file to put on the blighty.com webserver – creating that required copying and pasting two commands from one shell window to another. Then it created and gave me the new certificate and key. I copied those across to the webserver and reloaded it’s configuration. And I have TLS!
This is going to be very simple to completely automate, so you could easily build it in to existing automation to create TLS protected action and tracking links for branded domains. Supporting thousands of TLS protected hostnames wouldn’t be difficult.
And how about using the certificates for things other than webservers? Mail servers, say? You do need a webserver to be live while you’re generating or renewing a certificate – but that’s actually easier to do for a host that doesn’t usually serve web pages than one that does. Once the certificate is generated you can use it for any service, including mail servers.
ACME-movie
 

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Things you need to read: 2/5/16

gearheadAsk the Expert: How Can Email Marketers Stay Out of Gmail Jail and in the Inbox? The expert in question is an old friend of mine, Andrew Barrett. I met Andrew online in the late 90s, and we worked together (briefly) at MAPS. He was out of email for a while, but I’m pleased he came back to share his talents with us. The information in the article is valuable for anyone who struggles with getting to the Gmail inbox.
Unclutter Your Inbox, Archive & Keep Your Messages. Shiv Shankar talks about some new features at Yahoo Mail. With a simple click, you can archive email so it’s available to search, but not cluttering up your inbox. One of the things that jumped out at me from that article is that Yahoo is providing 1 TB of storage. That’s more than Google!
The EEC is doing a survey on the impact of CASL and want to hear from marketers. Go check out their blog post and take their survey.
Sparkpost has a guest blog from Alex Garcia-Tobar, co-founder of Valimail about common DKIM failures. I’ve met Alex a few times and I’ve always found him a pleasure to talk to. Alex is somewhat new in the email space, but he really gets some of the challenges in the authentication space. A lot of the issues he mentions in that blog post like lack of key rotation and shared keys are some of the technical debt I was talking about in my predictions for 2016 post.
What links have you read this week that are worth sharing?

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