The fact that I access a certain website is certainly visible to the admin in my office - i.e. at work - and to the ISPs at work, home or wherever I access that website from. But if I send an e-mail from Yahoo/Google/etc. are the sender and receiver visible to the said admin, considering the fact that the connection is thru https: ?
There's a few things to consider here:
Connecting to your service prover If you log on to https://mail.google.com or https://www.hotmail.com then you are over https and so should be secure.
However most corporates only have internet access through a proxy and like to virus scan traffic. As HTTPS traffic is encrypted they use so called man in the middle (MITM) proxies so when you connect to Gmail over https you actual connect to the proxy over https (and it provides a HTTPS certificate in Google's name) and then that proxy connects to Google.
This is allowed by web browsers if the proxy certificate is set up as a local CA on your computer (which if in such a corporate environment they will be able to install this), but is very difficult to do without access to your machine (e.g.on coffee shop wifi as you will get a HTTPS certificate error). While this sounds dodgy (and is not well liked by security professionals as can introduce more risks), it is quite common in larger companies - though often companies that do this also block access to web mail providers as well. Virus scanners installed on your machine work in the exact same way.
You can see if this is the case by looking at the HTTPS certificate change in your browser and see if it is the same as at home and chains up to a real certificate authority (CA) or to your company name.
Once a party is performing a MITM and, while most companies have neither the resources nor the inclination to read this traffic, other than to run it through an automatic virus scanner, in theory they can.
Encryption to the sender address. Once you are on your mail provider (via web mail or from an email client on your device) and send a mail, for example from your gmail account to a hotmail account you've got to consider whether that connection is encrypted. In 2026 Gmail started warning if the sender address is for a service that doesn't allow Gmail to use HTTPS to send it the message. Unfortunately that was pretty much the norm for a long time and in 2014 Google said 50% of mail it sends is unencrypted, though (partially in response to Gmail marking this as insecure I guess) that has increased to 80% at the time of writing.
Either way this is from Gmail servers so local admins (e.g. in your office) should not be able to intercept this traffic as it's not sent on the local network (unless you work for a network telco or a spy agency!), but in theory unencrypted messages could be read here.
User encrypted mail only encrypted the body. Technologies like PGP or SMIME allow you to Encrypt your email message separately before you send it via a provider but this is only for the message contents so the To Address, From Address and Subject are still visible over plain text SMIME does allow you to have different subjects but that has its own problems - see the answer here for more details). And it's a massive of a pain to use these to be honest.
Authentication technologies like do not help here When researching encrypted mail you may see mention of DMARC, DKIM and SPF but they are authentication methods (to ensure you sent the message) rather than tools to hide data so ignore any mention of those when asking about hiding data. For example the earlier Google Blog link talks about authentication as the other thing they will warn against.
Quote a broad topic, and not a great fit for a Stack Overflow question to be honest (perhaps would be OK on the sister site http://security.stackexchange.com), but hopefully that gives you some understanding anyway.
Another, more detailed answer, can be found here: Using SSL/TSL to secure your communications. What I understand summing up both answers is that the e-mail content should be encrypted separately to be completely safe. I still am not sure what the answer is re: e-mail adresses of the sender and the receiver(s).
I've noticed that the domain
contoso.com
is often used in documentation when a sample is needed. I always figured this was a dummy domain, used like the telephone prefix "555" to route spam into some kind of telecommunicative void (although contoso.com appears to be a real site).
Is there a domain I can safely use when I have to, say, test a registration form 20 times with a unique email address and I don't care what happens to the message, yet I don't want it going to a real person?
You can use example.com. According to the Wikipedia article:
example.com, example.net, and example.org are second-level domain names reserved by the Internet Engineering Task Force through RFC 2606, Section 3,1 for use in documentation and examples. They are not available for registration.
By implementing the reservation, the Internet Assigned Numbers Authority (IANA) made available domains to use in manuals and sample software configurations. Thus, documentation writers can be sure to select a domain name without creating naming conflicts if end-users try to use the sample configurations or examples verbatim.
When an address such as "yourusername#example.com" is used to demonstrate the sign-up process on a website, it indicates to the user they should fill in an actual e-mail address at which they receive mail. "example.com" is used in a generic and vendor-neutral manner.
These domain names resolve to a server managed by ICANN.
I started using whatever#example.com for this purpose, but then I began getting responses back from my outgoing email server saying delivery to that address had been delayed. I don't know about the OP, but I want something that I can send to and completely forget about it.
Now I'm changing over to whatever#mailinator.com -- I know that it gets delivered to their catchall (so I'm not getting any junk back about delivery errors), and if I like, I can even go check at http://mailinator.com/ to see if the email went through as planned. (But it's not clogging up my inbox if I don't care about it.)
http://www.faqs.org/rfcs/rfc2606.html has all the standard reserved names. Notably, example.com and the like started resolving a few years ago. Before that they were truly reserved names, not even found in DNS. But they are still useful "fake" domains.
A simple way of testing email delivery is to use Gmail with the "plus" rule. We use this when registering our shared email account with some services that use unique email addresses as the username. This enables us to use a single inbox for all of the incoming registrations and filter the messages to all go to the same folder.
http://fieldguide.gizmodo.com/how-to-use-the-infinite-number-of-email-addresses-gmail-1609458192
One trick you may or may not have picked up about Gmail is that you
can add in periods anywhere in the front part of your address and it
makes no difference whatsoever: john.smith#gmail.com works just the
same as johnsmith#gmail.com. What's more, you can add a plus sign and
any word before the # sign (e.g. johnsmith+hello#gmail.com) and
messages will still reach you. If these tweaks make no difference,
then why use them? One major reason: filters.
how about example.com?
It is a valid domain, but reserved by RFC to be used for documentation.
Contoso.com is a dummy domain that can be used for testing.
It's used by Microsoft as an example whenever they need an example company or domain. They're the ones who registered it, and they use it frequently in their examples, so I doubt they care if you use it for testing. They likely ignore anything that goes it seeing as how its posted all over the web and a likely target for spam.
Frankly, I utilize an email address from my own testing email server for this because part of the testing is to ensure that the form information actually gets to the email address, and since checking it is outside of my normal work-flow, that means I have to actively do so.
We are using .local domains for that.
For testing purposes I like to have e-mail addresses that really do not exist and cannot be registered. Even access by IANA like for example.com is a no-go for security reasons. Accidently sent e-mails to max.mustermann#example.com maybe be delivered to servers controlled by IANA. This maybe an privacy issue for Max Mustermann and so on ...
Do not treat me wrong: This is just for additional security minimizing the risks whereever possible.
guerillamail.com for example is blocked by several blacklists (like http://www.block-disposable-email.com). So maybe it's better to use contoso.com.
you could configure your in house MTA to discard all example.com/net/org emails. you can be sure that no one would expect them to be delivered. and that would save your server from using resources and wasting bandwidth.
If it's email you want to test, why not use a disposable email address, such as GuerrilaMail? You can send an email to anyone#guerrillamail.com, or set your own user name, for a limited amount of time.BTW, Contoso is a Microsoft dummy site they've been using to demo .Net technologies for a couple of years now.
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.