My team supports a website for a client, and we use SendGrid to send email related to the site on their behalf.
We do not have anything to do with their own email server and I don't at present know anything about it.
So far as I can work out, SendGrid has proper authentication and is an authorised sender for their domain, and almost 98% of email is delivered successfully.
However, we have had a handful of bounces with the reason "550 relaying denied" and all of these were to addresses at our client's domain (the same one as their website and the from address of the emails.)
Most emails to their domain were delivered successfully.
Unfortunately I don't have access to the full headers of the bounce emails, only the reason.
I understand that in general this error can either be caused by
the sender not being authenticated correctly. I am very far from being an expert in this but so far as I can tell, there is nothing wrong there. Or
a DNS or similar misconfiguration on the part of the recipient's email domain. I have even less understanding about this and I have no access or responsibility for the client's email server.
My main question is, is there any way the domain being the same as the from address could be related? Being as the email is claiming to be from the same place it's sent to, is it possible for that to affect how it's handled by relays?
If not, I'd also appreciate any pointers on where to look for the issue (or what to advise the client to look at if the problem is likely to be from their end.) I have been trying to research issues with email configuration and authentication but I am very much a novice in this area.
Thanks in advance.
The domain being the same could very well be related, but normally when that happens, the receiving server refuses all mail purporting to be from itself.
Separate from DKIM & SPF, most mail servers believe they alone are responsible for the mail from their domain.com. As such, a lot of them have anti-phishing filters that reject "outside" mail that claims to be from themselves. It's like "You can't be Carrie, I'm Carrie! Go Away!"
The fact that it's only some mail is interesting. The error being relay denied may also be key, though these anti-phishing filters often use "fake" errors to not give away the game.
Do the recipients of the messages that are being rejected have some kind of internal forwarding applied? That may be the cause, in which case that bounce reason is honest.
Or they may have a more defined anti-phishing feature, only rejecting mail From or For certain addresses. You can try testing certain combinations, and see if anything is repeatable.
Ultimately however, it will come down to working with the receiving mail domain's admin, and either updating those rules, or whitelisting the SendGrid IPs that are sending the mail to them.
I am build a tool that initiates an SMTP transaction with a domain to see if (a) that domain can receive emails and (b) the desired address exists on that domain. I will be batching large groups of email addresses (10,000+ at a time), but I don't want to bombard the server and get blacklisted. Are there guidelines for how often is it safe to communicate with an SMTP server?
I know about the VRFY command, but it is not implemented across the board. I plan to attempt to use the VRFY command and fall back to using,
MAIL From:<user#example.com>
RCPT To:<first.last#example.org>
QUIT
to see if the message will be deliverable. Again, are there guidelines on how often I can initiate an SMTP transaction like this on a domain?
Edit:
The purpose of this is to create a tool that my organization can use to (a) clean some bad emails from several largely inactive lists so that we do not have to pay our email delivery system to send potentially thousands of emails that will bounce, and (b) check an email when a user subscribes to a list so that we reject emails like aoghuifdgsiuvb#gmail.com.
First of all, spamming is bad. Always ask user wheter she wants to receive newsletters.
"Unsort" mail addresses by domain, leaving the "distance" between e-mail addresses with same domain as big possible.
I think it's not the programmer's decision. There should be a config value which tells a minimum amount of time between two mail sending to the same domain. You should set up a limit also for that config value, avoid setting it to zero or low value.
The only universal guideline I believe can be offered is "don't do this". If you behave like a spammer, you will be treated like a spammer. In the optimistic scenario, sites will already have controls in place, and silently throttle or block you. In less ideal scenarios, they will initiate actions against you on the (reasonable) assumption that you are collecting addresses for a spam list.
A better soluton would be to actually follow through the whole SMTP session, sending a user an email with a verification code/link. This has the advantage of showing that the user actually has control of the address in question and it keeps you from looking like a spam bot.
Volume is not as much the issue as reputation. Let the user know you're about to send them an email in your web flow. This means they're much less likely to mark it as spam.
some hosts have clear and defined guidelines as to how many emails can be sent per hour.
So i guess this would depned onyour hostng service provider, UNLESS your hosting your own mail server off course.
We are building a system that is, effectively, an email/calendar/contact client.
Users will provide us with their email address password (or other auth, eg oauth) and we will connect to their underlying email system.
"underlying systems" include:
Microsoft Exchange / Office365
GMail
Yahoo Mail
Apple email
Generic IMAP
Each of these systems have subtle (and not so subtle) differences in their APIs, especially to access calendar & contact data. Thus we need to know what provider the user is using.
But we would rather not ASK the user. We would like to figure it out (and at, least reduce the choices) automatically.
I've looked around for something that already implements this but have not found anything. I know it's mostly possible because Windows Phone does it pretty well (just enter username/pw and it does the right thing).
Before I dive in and start writing my own I want to ensure I'm not wasting my time if someone's already done it in an excellent way.
Know of anything like this? For this project prefer C#/.NET.
[EDIT: Adding potential algo]
Potential Algorithm:
Given email address & password
Extract domain name from email address
Try Exchange autodiscover. If successful done.
Use DNS MX records to find smtp host.
Do SMTP EHLO
Gmail responds with "250-mx.google.com at your service"
So if we see a "google.com" we are done.
Yahoo responds with 250-mta1257.mail.sk1.yahoo.com
So if we see a "yahoo.com" in the response we are done.
Apple responds with 250-xxxxxx-mac.com
So if we see a "mac.com" in the response we are done.
If none of the above
IMAP?
...
[EDIT: 5/18]
I built a prototype that uses methods that don't require auth (e.g. just MX/SMTP sluthing). Give it a try: http://bit.ly/KLZKxD
Algorithm seems reasonable. You will get best results running from unfiltered server (meaning it has direct SMTP outbound / doesn't run through a proxy). If running from client (mobile/tablet/desktop), then no guarantees as some ISP's pass SMTP through a proxy relay hence EHLO response is only for proxy.
You may want to do a port check for servers to verify expected protocol support (just a TCP connect may be sufficient but protocol handshake is preferable). Additionally, best to build up a database of verified SMTP and IMAP server mappings as there can be split names (e.g. smtp.domain.com and mail.domain.com) - discovering SMTP is easy, discovering outbound server(s) which usually also means calendar/contacts server, not so much (except for Exchange but only if autodiscovery is configured correctly).
If you can get your users to approve and assuming you have their username/password, you could try connecting to SMTP via MX record and sending an email back to your own address then checking through headers for useful info about the server (needs to be authenticated to relay). Users could alternatively reply to an email you generate in order to get the same server info.
Also ensure that you do your own DNS query and try each MX record or all primaries -- if the principal MX is down or DNS is poorly configured for equal weighting, you could end up hitting a smarthost / backup which may just be a dumb SMTP relay / store-and-forward and not give you the correct response.
TL;DR: No quick solution but a cascaded algorithm that trys and fails different solutions until one works / gives an expected result should work.
Most devices can auto detect the service by parsing the Whole e-mail address. Xyz#gmail.com would obviously be a gmail account. So for Apple, Gmail, Yahoo, Live, Hotmail etc you can easily program for.
For other domains, including custom, you can try this: http://www.exclamationsoft.com/exclamationsoft/netmailbot/help/website/HowToFindTheSMTPMailServerForAnEmailAddress.html
You can detect Google Apps For Your Domain accounts by examining the domain's MX records. If the primary MX record is ASPMX.L.GOOGLE.com, then it's GMail.
I created an implementation of this that has been used widely with some success: https://github.com/tig/Email2Calendar
This is used by both milelogr.com and freebusy.io.
I use an email registration and confirmation in my project (yes, I know about OpenID. In my counry, a main email service lacks it).
Sometimes users misspell their email addresses. I know about this due to "message could not be delivered" letters in a mailbox. A misspelled address is absolutely correct, because I check it with a regular expression - say, jon.doe#example.com intstead of john.doe#example.com. And I do not want to duplicate a email field in a registration form (who likes it?).
Request processing routine cannot wait for email delivery - it could take an unpredictable time. So, my script will return to user a confirmation message "An email was sent". And the user will wait for it forever (of cause, not - he/she will turn to an alternative project with a more perfect registration system).
Does someone knows how it can be improved (in any programming language)?
If you cannot wait for a response back from a confirmation e-mail, I would display a yes/no message box confirming their e-mail (i.e Send e-mail to jon.doe#example.com?) before sending the e-mail. While your at it, you can check to see if the e-mail is a duplicate as well.
If no duplicate found and they click "Yes" then send the e-mail. If not, ask them to re-enter the e-mail address.
With this approach you have gone above and beyond validating correct e-mail addresses since there are no services that will explicitly check for correct/valid addresses.
Unfortunately, there's no canonical way to spell anything in an e-mail address and no way to check programmatically whether it's spelled correctly or not. The only tool that can confirm the correctness of a valid e-mail address is Eyeball 1.0, which runs client side.
You can try the SMTP VRFY on the server but most won't reply with anything valuable. Most will simply say "go ahead and try it" because returning something useful would be invaluable to spammers.
You can always check the domain name with a DNS lookup but the only way to check an email address is to send a message.
Try to have the user type his email twice with an email confirmation field (as for the password).
EDIT : Anthony's idea is good too.
For user parts of email the only thing I can think of is using:
MX lookups (if mail provider doesn't block them... since that can be abused to filter email lists)
Requiring user to enter email twice to ensure he doesn't misspell user portion of email
As for domain part of email, take a look at this:
AngularJs directive to offer suggestions for misspelled emails?
It helped me to reduce bounce for misspellings like gmai.com and gmail.con.
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.