I've implemented List-Unsubscribe (RFC 2369) for marketing emails we send. I am providing both an unsubscribe email address and an unsubscribe URL. An example of a generated header looks like this:
List-Unsubscribe: <mailto:unsubscribe#myserver.com?subject=unsubscribe>, <https://myserver.com/unsubscribe?email=recipient#email.com>
In the past few email campaigns we've done, it has worked great. There's only one problem. Sometimes we receive unsubscribe requests from email addresses we didn't actually send mail to. I think this happens when the user has multiple email addresses and the email we send is forwarded to some other destination. So we send to user-a#email.com, but the recipient opens it at user-b#email.com. When they click the "Unsubscribe" link provided by their email client, it generates an email to us telling us to unsubscribe user-b#email.com.
Sometimes we can find the intended address if the address we sent to was very similar, or if the user has a unique name, but sometimes it's impossible to determine which email address we should unsubscribe. That's frustrating because we know the user will be upset if they receive another email from us in the future.
I tried to fix this by adding a unique identifier to the subject line, so that a subject looks like unsubscribe_20934832034820348, but when we do that, email clients stop showing the Unsubscribe button. It's as if they will only show the Unsubscribe button if the subject line is exactly "unsubscribe".
I didn't see anything in the RFC about the subject line needing to take a particular form, and we are also taking care not to put the user's email address directly in the subject line. (It is a hashed combination of their email address and a portion of the original message, making it unique across all emails we send.)
Is there some sort of convention around this? If so, how can I reliably determine the original address we sent to when we receive unsubscribe emails?
It looks like there is no problem using this sort of subject line. However, it seems that each email client decides in its own proprietary way when and how to display the Unsubscribe button/link, and it does seem that that when you change from a simple "unsubscribe" to "unsubscribe" plus some unique identifier, some clients might subject you to some sort of test period before showing the link to users. In my testing, Gmail did not show me the link when sending small batches of test emails, but after I sent a large batch of emails, the link did start appearing, and I did indeed receive the generated unsubscribe mails properly.
I hope this helps someone out there.
I am trying to send a spoofed email using gmail. before people freak out, no I am not spamming anybody (if you have to know why, an explanation is below). Using this question and answer, I was able to send a test email to myself with a spoofed to address (it appeared as I wanted), however, regardless of what I enter in the MAIL FROM field or the From: field in the DATA, it always appears from the address I used to authenticate.
My question is whether it's possible to spoof the from address as well. The goal would be for the from address to appear as something other than an email address. (again, explanation is below)
EXPLANATION
For those who want to know why I am doing this, my brother recently got promoted, and he and I are both fans of the show How I Met Your Mother. As such, I would like to send him a The Bro Code approved congratulatory email, which is required to be of the form:
To: Bro
From: Bro
Subject: Bro!
Nice, Bro!
Therefore, I need the From address to appear to be simply "Bro"
I believe the short answer is no.
Email headers are just text, so if you are using sendmail or something, you can use whatever you want. However, it might (see: will likely) end up in his spam folder.
Gmail needs to protect it's reputation, so they will always add a breadcrumb to say who actually sent the email. For instance, you can setup gmail to send email "from" non-gmail addresses, but the message will be sent from your gmail address "on behalf" of your non-gmail address.
My application server needs to notify users about some events via email. Usually there will be between 10-100 users to whom the notifications should be sent, but there may be a few cases where there may be a bit more (I don't think it will ever be more than 1000).
What is the best practice in such cases? Should I send a single email per user or one email with all users as recipients or group users and send one email for each group (for example 1 email for 10 users)? If it makes any difference I may add that I am using System.Net.Mail to send emails.
Thanks in advance for your suggestions
Lukasz Glaz
You should send one e-mail per user.
The alternatives either involve putting e-mails in BCC (which will increase your chances of having your mails flagged as spam), or revealing your user A's e-mail address to user B, where user A and user B are in the same "group".
You need to check with your smtp server manager - to avoid being blocked.
if you own the smtp server, than this is not a problem.
I think the best way is to send them in bulks of 50 recipients per message (it will be a little faster than one by one).
I wouldn't definetly put all recipients into a To: field. Even from one place. It's just not a good practice to show other's addresses. And it generates a problem when someone hits "Reply All" and suddenly mails all others with his crap :)
If you own the smtp server, and your application server -> smtp server connection isn't slow, I would just send every mail individually, with each single recipient in To: field. It just looks much less spam'ish then getting a mail with empty (or some bogus) To: field and being in BCC only.
Other advantage is the person recieving your mail will know what email address is used. I got plenty of them, use different ones in different places, and it helps to be able to see which one I used on which site (sometimes I need to use this address for password reset / login, and I forgot, and if all mails had me in BCC, I'm screwed). This is from your user's perspective.
This is a tricky one and I've always relied on techniques, such as permission-based emails (i.e. only sending to people you have permission to send to) and not using blatantly spamish terminology.
Of late, some of the emails I send out programmatically have started being shuffled into people's spam folder automatically and I'm wondering what I can do about it.
This is despite the fact that these particular emails are not ones that humans would mark as spam, specifically, they are emails that contain license keys that people have paid good money for, so I don't think they're going to consider them spam
I figure this is a big topic in which I am essentially an ignorant simpleton.
Use email authentication methods, such as SPF, and DKIM to prove that your emails and your domain name belong together, and to prevent spoofing of your domain name. The SPF website includes a wizard to generate the DNS information for your site.
Check your reverse DNS to make sure the IP address of your mail server points to the domain name that you use for sending mail.
Make sure that the IP-address that you're using is not on a blacklist
Make sure that the reply-to address is a valid, existing address.
Use the full, real name of the addressee in the To field, not just the email-address (e.g. "John Smith" <john#blacksmiths-international.com> ).
Monitor your abuse accounts, such as abuse#yourdomain.example and postmaster#yourdomain.example. That means - make sure that these accounts exist, read what's sent to them, and act on complaints.
Finally, make it really easy to unsubscribe. Otherwise, your users will unsubscribe by pressing the spam button, and that will affect your reputation.
That said, getting Hotmail to accept your emails remains a black art.
Sign up for an account on as many major email providers as possible (gmail/yahoo/hotmail/aol/etc). If you make changes to your emails, either major rewording, changes to the code that sends the emails, changes to your email servers, etc, make sure to send test messages to all your accounts and verify that they are not being marked as spam.
A few bullet points from a previous answer:
Most important: Does the sender address ("From") belong to a domain that runs on the server you send the E-Mail from? If not, make it so. Never use sender addresses like xxx#gmail.com. User reply-to if you need replies to arrive at a different address.
Is your server on a blacklist (e.g. check IP on spamhaus.org)? This is a possibility when you're on shared hosting when neighbours behave badly.
Are mails filtered by a spam filter? Open an account with a freemailer that has a spam folder and find out. Also, try sending mail to an address without any spam filtering at all.
Do you possibly need the fifth parameter "-f" of mail() to add a sender address? (See mail() command in the PHP manual)
If you have access to log files, check those, of course.
Do you check the "from:" address for possible bounce mails ("Returned to sender")? You can also set up a separate "errors-to" address.
You can tell your users to add your From address to their contacts when they complete their order, which, if they do so, will help a lot.
Otherwise, I would try to get a log from some of your users. Sometimes they have details about why it was flagged as spam in the headers of the message, which you could use to tweak the text.
Other things you can try:
Put your site name or address in the subject
Keep all links in the message pointing to your domain (and not email.com)
Put an address or other contact information in the email
Confirm that you have the correct email address before sending out emails. If someone gives the wrong email address on sign-up, beat them over the head about it ASAP.
Always include clear "how to unsubscribe" information in EVERY email. Do not require the user to login to unsubscribe, it should be a unique url for 1-click unsubscribe.
This will prevent people from marking your mails as spam because "unsubscribing" is too hard.
In addition to all of the other answers, if you are sending HTML emails that contain URLs as linking text, make sure that the URL matches the linking text. I know that Thunderbird automatically flags them as being a scam if not.
The wrong way:
Go to your account now: http://www.paypal.com
The right way:
Go to your account now: http://www.yourdomain.org
Or use an unrelated linking text instead of a URL:
Click here to go to your account
You may consider a third party email service who handles delivery issues:
Exact Target
Vertical Response
Constant Contact
Campaign Monitor
Emma
Return Path
IntelliContact
SilverPop
Delivering email can be like black magic sometimes. The reverse DNS is really important.
I have found it to be very helpful to carefully track NDRs. I direct all of my NDRs to a single address and I have a windows service parsing them out (Google ListNanny). I put as much information from the NDR as I can into a database, and then I run reports on it to see if I have suddenly started getting blocked by a certain domain. Also, you should avoid sending emails to addresses that were previously marked as NDR, because that's generally a good indication of spam.
If you need to send out a bunch of customer service emails at once, it's best to put a delay in between each one, because if you send too many nearly identical emails to one domain at a time, you are sure to wind up on their blacklist.
Some domains are just impossible to deliver to sometimes. Comcast.net is the worst.
Make sure your IPs aren't listed on sites like http://www.mxtoolbox.com/blacklists.aspx.
I hate to tell you, but I and others may be using white-list defaults to control our filtering of spam.
This means that all e-mail from an unknown source is automatically spam and diverted into a spam folder. (I don't let my e-mail service delete spam, because I want to always review the arrivals for false positives, something that is pretty easy to do by a quick scan of the folder.)
I even have e-mail from myself go to the spam bucket because (1) I usually don't send e-mail to myself and (2) there are spammers that fake my return address in spam sent to me.
So to get out of the spam designation, I have to consider that your mail might be legitimate (from sender and subject information) and open it first in plaintext (my default for all incoming mail, spam or not) to see if it is legitimate. My spam folder will not use any links in e-mails so I am protected against tricky image links and other misbehavior.
If I want future arrivals from the same source to go to my in box and not be diverted for spam review, I will specify that to my e-mail client. For those organizations that use bulk-mail forwarders and unique sender addresses per mail piece, that's too bad. They never get my approval and always show up in my spam folder, and if I'm busy I will never look at them.
Finally, if an e-mail is not legible in plaintext, even when sent as HTML, I am likely to just delete it unless it is something that I know is of interest to me by virtue of the source and previous valuable experiences.
As you can see, it is ultimately under an users control and there is no automated act that will convince such a system that your mail is legitimate from its structure alone. In this case, you need to play nice, don't do anything that is similar to phishing, and make it easy for users willing to trust your mail to add you to their white list.
one of my application's emails was constantly being tagged as spam. it was html with a single link, which i sent as html in the body with a text/html content type.
my most successful resolution to this problem was to compose the email so it looked like it was generated by an email client.
i changed the email to be a multipart/alternative mime document and i now generate both text/plain and text/html parts.
the email no longer is detected as junk by outlook.
Yahoo uses a method called Sender ID, which can be configured at The SPF Setup Wizard and entered in to your DNS. Also one of the important ones for Exchange, Hotmail, AOL, Yahoo, and others is to have a Reverse DNS for your domain. Those will knock out most of the issues. However you can never prevent a person intentionally blocking your or custom rules.
You need a reverse DNS entry. You need to not send the same content to the same user twice. You need to test it with some common webmail and email clients.
Personally I ran mine through a freshly installed spam assassin, a trained spam assassin, and multiple hotmail, gmail, and aol accounts.
But have you seen that spam that doesn't seem to link to or advertise anything? That's a spammer trying to affect your Bayesian filter. If he can get a high rating and then include some words that would be in his future emails it might be automatically learned as good. So you can't really guess what a user's filter is going to be set as at the time of your mailing.
Lastly, I did not sort my list by the domains, but randomized it.
I've found that using the recipients real first and last name in the body is a sure fire way of getting through a spam filter.
In the UK it's also best practice to include a real physical address for your company and its registered number.
That way it's all open and honest and they're less likely to manually mark it as spam.
I would add :
Provide real unsubscription upon click on "Unsubscribe". I've seen real newsletters providing a dummy unsubscription link that upon click shows " has been unsubscribed successfully" but I will still receive further newsletters.
The most important thing you can do is to make sure that the people you are sending email to are not likely going to hit the "Spam" button when they receive your email. So, stick to the following rules of thumb:
Make sure you have permission from the people you are sending email to. Don't ever send email to someone who did not request it from you.
Clearly identify who you are right at the top of each message, and why the person is receiving the email.
At least once a month, send out a reminder email to people on your list (if you are running a list), forcing them to opt back in to the list in order to keep receiving communications from you. Yes, this will mean your list gets shorter over time, but the up-side is that the people on your list are "bought in" and will be less likely to flag your email.
Keep your content highly relevant and useful.
Give people an easy way to opt out of further communications.
Use an email sending service like SendGrid that works hard to maintain a good IP reputation.
Avoid using short links - these are often blacklisted.
Following these rules of thumb will go a long way.
I have had the same problem in the past on many sites I have done here at work. The only guaranteed method of making sure the user gets the email is to advise the user to add you to there safe list. Any other method is really only going to be something that can help with it and isn't guaranteed.
It could very well be the case that people who sign up for your service are entering emails with typing mistakes that you do not correct. For example: chris#gmial.com -or- james#hotnail.com.
And such domains are configured to be used as spamtraps which will automatically flag your email server's IP and/or domain and hurt its reputation.
To avoid this, do a double-check for the email address that is entered upon your product subscription. Also, send a confirmation email to really ensure that this email address is 100% validated by a human being that is entering the confirmation email, before you send them the product key or accept their subscription. The verification email should require the recipient to click a link or reply in order to really confirm that the owner of the mailbox is the person who signed up.
It sounds like you are depending on some feedback to determine what is getting stuck on the receiving end. You should be checking the outbound mail yourself for obvious "spaminess".
Buy any decent spam control system, and send your outbound mail through it. If you send any decent volume of mail, you should be doing this anyhow, because of the risk of sending outbound viruses, especially if you have desktop windows users.
Proofpoint had spam + anti-virus + some reputation services in a single deployment, for example. (I used to work there, so I happen to know this off the top of my head. I'm sure other vendors in this space have similar features.) But you get the idea. If you send your mail through a basic commerical spam control setup, and it doesn't pass, it shouldn't be going out of your network.
Also, there are some companies that can assist you with increasing delivery rates of non-spam, outbound email, like Habeas.
Google has a tool and guidelines for this. You can find them on: https://postmaster.google.com/ Register and verify your domain name and Google provides an individual scoring of that IP-address and domain.
From the bulk senders guidelines:
Authentication ensures that your messages can be correctly classified. Emails that lack authentication are likely to be rejected or placed in the spam folder, given the high likelihood that they are forged messages used for phishing scams. In addition, unauthenticated emails with attachments may be outrightly rejected, for security reasons.
To ensure that Gmail can identify you:
Use a consistent IP address to send bulk mail.
Keep valid reverse DNS records for the IP address(es) from which you send mail, pointing to your domain.
Use the same address in the 'From:' header on every bulk mail you send.
We also recommend the following:
Sign messages with DKIM. We do not authenticate messages signed with keys using fewer than 1024 bits.
Publish an SPF record.
Publish a DMARC policy.
I always use:
https://www.mail-tester.com/
It gives me feedback on the technical part of sending an e-mail. Like SPF-records, DKIM, Spamassassin score and so on. Even though I know what is required, I continuously make errors and mail-tester.com makes it easy to figure out what could be wrong.
First of all, you need to ensure the required email authentication mechanisms like SPF and DKIM are in place. These two are prominent ways of proving that you were the actual sender of an email and it's not really spoofed. This reduces the chances of emails getting filtered as spam.
Second thing is, you can check the reverse DNS output of your domain name against different DNSBLs. Use below simple command on terminal:
**dig a +short (domain-name).(blacklist-domain-name)**
ie. dig a +short example.com.dsn.rfc-clueless.org
> 127.0.0.2
In the above examples, this means your domain "example.com" is listed in blacklist but due to Domain Setting Compliance(rfc-clueless.org list domain which has compliance issue )
note: I prefer multivalley and pepipost tool for checking the domain listings.
The from address/reply-to-id should be proper, always use visible unsubscribe button within your email body (this will help your users to sign out from your email-list without killing your domain reputation)
The intend of most of the programmatically generated emails is generally transactional, triggered or alert n nature- which means these are important emails which should never land into spam.
Having said that there are multiple parameters which are been considered before flagging an email as spam. While Quality of email list is the most important parameter to be considered, but I am skipping that here from the discussion because here we are talking about important emails which are sent to either ourself or to known email addresses.
Apart from list quality, the other 3 important parameters are;
Sender Reputation
Compliance with Email Standards and Authentication (SPF, DKIM, DMARC, rDNS)
Email content
Sender Reputation = Reputation of Sending IP address + Reputation of Return Path/Envelope domain + Reputation of From Domain.
There is no straight answer to what is your Sender Reputation. This is because there are multiple authorities like SenderScore, Reputation Authority and so on who maintains the reputation score for your domain. Apart from that ISPs like Gmail, Yahoo, Outlook also maintains the reputation of each domain at their end.
But, you can use free tools like GradeMyEmail to get a 360-degree view of your reputation and potential problems with your email settings or any other compliance-related issue too.
Sometimes, if you're using a new domain for sending an email, then those are also found to land in spam. You should be checking whether your domain is listed on any of the global blocklists or not. Again GradeMyEmail and MultiRBL are useful tools to identify the list of blocklists.
Once you're pretty sure with the sender reputation score, you should check whether your email sending domain complies with all email authentications and standards.
SPF
DKIM
DMARC
Reverse DNS
For this, you can again use GradeMyEmail or MXToolbox to know the potential problems with your authentication.
Your SPF, DKIM and DMARC should always PASS to ensure, your emails are complying with the standard email authentications.
Here's an example of how these authentications should look like in Gmail:
Similarly, you can use tools like Mail-Tester which scans the complete email content and tells the potential keywords which can trigger spam filters.
To allow DMARC checks for SPF to pass and also be aligned when using sendmail, make sure you are setting the envelope sender address (-f or -r parameter) to something that matches the domain in the From: header address.
With PHP:
Using PHP's built-in mail() function without setting the 5th paramater will cause DMARC SPF checks to be unaligned if not done correctly. By default, sendmail will send the email with the webserver's user as the RFC5321.MailFrom / Return Path header.
For example, say you are hosting your website domain.com on the host.com web server. If you do not set the additional parameters parameter:
mail($to,$subject,$message,$headers); // Wrong way
The email recipient will receive an email with the following mail headers:
Return-Path: <your-website-user#server.host.com>
From: <your-website-user#domain.com>
Even though this passes SPF checks, it will be unaligned (since domain.com and host.com do not match), which means that DMARC SPF check will fail as unaligned.
Instead, you must pass the envelope sender address to sendmail by including the 5th parameter in the PHP mail() function, for example:
mail($to,$subject,$message,$headers, '-r bounce_email#domain.com'); // Right way
In this case, the email recipient will receive an email with the following mail headers:
Return-Path: <bounce_email#domain.com>
From: <your-website-user#domain.com>
Since both of these headers contain addresses from domain.com, SPF will pass and also be aligned, which means that DMARC will also pass the SPF check.