Using Reply-To:

Yesterday I learned that some ESPs don’t support the reply to: address. I asked around to discover which ESPs did. Here’s what I learned.

ESPs that support reply-to:

ActiveCampaign
AmazonSES
ConstantContact
Campaign Monitor
Cordial
Delivra
DoList
Eloqua
Emma
Epsilon
GetResponse
HubSpot
iContact
Listrak
Mailkit
MailUp
Marketo
N6
Pardotword
Responsys
Sailthru
SFMC
Sharpspring
Twilio / SendGrid
Zeta Global

Thanks to all the colleagues who answered my question.

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M3AAWG Recommends TLS

SSL or Secure Sockets Layer is protocol designed to provide a secure way of transmitting information between computer systems. Originally created by Netscape and released publicly as SSLv2 in 1995 and updated to SSLv3 in 1996. TLS or Transport Layer Security was created in 1999 as a replacement for SSLv3. TLS and SSL are most commonly used to create a secure (encrypted) connection between your web browser and websites so that you can transmit sensitive information like login credentials, passwords, and credit card numbers.
M3AAWG published a initial recommendation that urges the disabling of all versions of SSL. It has been a rough year for encryption security, first with Heartbleed vulnerability with the OpenSSL library, and again with POODLE which stands for “Padding Oracle on Downgraded Legacy Encryption” that was discovered by Google security researchers in October of 2014. On December 8, 2014 it was reported that TLS implementations are also vulnerable to POODLE attack, however unlike SSLv3, TLS can be patched where as SSL 3.0 has a fundamental issue with the protocol.

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PTR Records

PTR records are easy to over look and they have a significant impact on your ability to deliver mail without them.  Some ISP and mailbox providers will reject mail from IP addresses that do not have a PTR record created. PTR records are a type of DNS record that resolves an IP address to a fully qualified domain name or FQDN.  The PTR records are also called Reverse DNS records. If you are sending mail on a shared IP address, you’ll want to check to make sure the PTR record is setup, however you most likely will not be able to change it.  If you are on a dedicated IP address or using a hosting provider like Rackspace or Amazon AWS, you’ll want to create or change the PTR records to reflect your domain name.
We usually think about DNS records resolving a domain name such as www.wordtothewise.com to an IP address.  A query for www.wordtothewise.com is sent to a DNS server and the server checks for a matching record and returns the IP address of 184.105.179.167.  The A record for www is stored within the zone file for wordtothewise.com.  PTR records are not stored within your domain zonefile, they are stored in a zonefile usually managed by your service provider or network provider.
Some service providers provide an interface where you can create the PTR record yourself, others require you to submit a support request to create or change the PTR record.
If you know what IP address you are sending mail from, use our web based DNS tool to check if you have a PTR record created.
http://tools.wordtothewise.com/dns
Checking for a PTR record for 184.105.179.167 returns
167.128-25.179.105.184.in-addr.arpa 3600 PTR webprod.wordtothewise.com.
If you received Response: NXDOMAIN (There is no record of any type for x.x.x.x.in-addr.arpa), this means you’re missing the PTR record and need to create one ASAP if you are sending mail from that IP address!

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Ad-hoc analysis

I often pull emails into a database to analyze them, but sometimes I want something simpler. Emails are typically stored in one of two ways: mbox format, where an entire mailbox is stored in a single file, and maildir format, where a mailbox is a directory with one file in it for each email.
My desktop mail application is Mail.app on OS X, and it stores messages in a maildir-ish format, so I’m going to work with that here. If you’re using mbox format mailboxes it’s a little trickier (but you can use a tool called formmail to split an mbox style format into a maildir directory and go from there).
I want to gather some statistics on mail I’ve sent to abuse desks, so the first thing I do is open up a terminal window and change directory to where my “Sent Messages” mailbox is:
cd Library/Mail/V2/IMAP-steve@misc.wordtothewise.com/Sent Messages.mbox
(Tab completion is really useful for navigating through the mailbox hierarchy.)
Then I need to go through every email (file) in that directory, for each file find the “To:” header and check to see if it was sent to an abuse desk. If it was sent to an abuse desk I want to find the email address for each one, count how many times I see that email address and find the top twenty or so abuse desks I send reports to. I can do all that with a single command line:
find . -type f -exec egrep -m1 '^To:' {} ; | egrep -o 'abuse@[a-zA-Z0-9._-]+' | sort | uniq -c | sort -nr | head -20
(Enter that all as a single line, even though it’s wrapped into two here).
That’s a bit much to understand all at once, so lets redo that in several stages, with an intermediate file so we can see what’s going on.
find . -type f -exec egrep -m1 '^To:' {} ; >tolines.txt
The find command finds all the files in a directory and does something with them. In this case we start looking in the current directory (“.”), look just for files (“-type f”) and for each file we find we run that file through another command (“-exec egrep -m1 ‘^To:’ {} ;”) and write the result of that command to a file (“>tolines.txt”). The egrep command we run for each file goes through the file and prints out the first (“-m1”) line it finds that begins with “To:” (“‘^To:'”). If you run that and take a look at the file it creates you can see one line for each message, containing the “To:” header (or at least the first line of it).
The next thing to do is to go through that and pull out just the email addresses – and just the ones that are sent to abuse desks:
egrep -o 'abuse@[a-zA-Z0-9._-]+' tolines.txt
This uses egrep a second time, this time to look for lines that look like an email address (“‘abuse@[a-zA-Z0-9._-]+'”) and when it finds one print out just the part of the line that matched the pattern (“-o”).
Running that gives us one line of output for each email we’re interested in, containing the address it was sent to. Next we want to count how many times we see each one. There’s a command line idiom for that:
egrep -o 'abuse@[a-zA-Z0-9._-]+' tolines.txt | sort | uniq -c
This takes all the lines and sorts (“sort”, reasonably enough) them – so that identical lines will be next to each other – then counts runs of identical lines (“uniq -c”). We’re nearly there – the result of this is a count and an email address on each line. We just need to find the top 20:
egrep -o 'abuse@[a-zA-Z0-9._-]+' tolines.txt | sort | uniq -c | sort -nr | head -20
Each line begins with the count, so we can use sort again, this time telling it to sort by number, high to low (“sort -nr”). Finally, “head -20” will print just the first 20 lines of the result.
The final result is this:

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