A number of applications have the handy feature of allowing users to respond to notification emails from the application. The responses are slurped back into the application.
For example, if you were building a customer support system the email would likely contain some token to link the response back to the correct service ticket.
What are some guidelines, hints and tips for implementing this type of system? What are some potential pitfalls to be aware of? Hopefully those who have implemented systems like this can share their wisdom.
Some guidelines and considerations:
The address question: The best thing to do is to use the "+" extension part of an email (myaddr**+custom**#gmail.com) address. This makes it easier to route, but most of all, easier to keep track of the address routing to your system. Other techniques might use a token in the subject
Spam: Do spam processing outside the app, and have the app filter based on a header.
Queuing failed messages: Don't, for the most part. The standard email behavior is to try for up to 3 days to deliver a message. For an application email server, all this does is create giant spool files of mail you'll most likely never process. Only queue messages if the failure reasons are out of your control (e.g., server is down).
Invalid message handling: There are a multiple of ways a message can be invalid. Some are limitations of the library (it can't parse the address, even though its an RFC valid one). Others are because of broken clients (e.g., omitting quotes around certain headers). Other's might be too large, or use an unknown encoding, be missing critical headers, have multiple values where there should only be one, violate some semantic specific to your application, etc, etc, etc. Basically, where ever the Java mail API could throw an exception is an error handling case you must determine how to appropriately handle.
Error responses: Not every error deserves a response. Some are generated because of spam, and you should avoid sending messages back to those addresses. Others are from automated systems (yourself, a vacation responder, another application mail system, etc), and if you reply, it'll send you another message, repeating the cycle.
Client-specific hacks: like above, each client has little differences that'll complicate your code. Keep this in mind anytime you traverse the structure of a message.
Senders, replies, and loops: Depending on your situation, you might receive mail from some of the following sources:
Real people, maybe from external sources
Mailing lists
Yourself, or one of your own recipient addresses
Other mail servers (bounces, failures, etc)
Entity in another system (my-ldap-group#company.com, system-monitor#localhost)
An automated system
An alias to one of the above
An alias to an alias
Now, your first instinct is probably "Only accept mail from correct sources!", but that'll cause you lots of headaches down the line because people will send the damnedest things to an application mail server. I find its better to accept everything and explicitly deny the exceptions.
Debugging: Save a copy of the headers of any message you receive. This will help out tremendously anytime you have a problem.
--Edit--
I bought the book, Building Scalable Web Sites, mentioned by rossfabricant. It -does- have a good email section. A couple of important points it has are about handling email from wireless carriers and authentication of emails.
You can set the address that the email is sent from, what will be put into the To: address if someone just presses 'Reply-to'. Make that unique, and you'll be able to tell where it came from, and to where it must be directed back to.
When it comes to putting a name beside it though '"something here" ' - put something inviting to have them just reply to the mail. I've seen one major web-app, with Email capturing that has 'do not reply', which turns people off from actually sending anything to it though.
Building Scalable Web sites has a nice section on handling email. It's written by a Flickr developer.
(source: lsl.com.au)
EDIT: I misunderstood your question.
You could configure your email server to catch-all, and generate a unique reply-to address. E.g. CST-2343434#example.com.
A polling process on the server could read the inbox and parse out the relevant part from the received email, CS-2343434 could mean Customer Support ticket ID no. 2343434.
I implemented something like this using JavaMail API.
Just a thought.
The best way to achieve this will be to write a window service that acts like a mail client [pop3 or imap]. This windows service should execute a timed action triggered by a timer, which connects to the mail server and polls the server for any unread message(s) available in the email inbox. The email ID to check for is the email ID on which the users will give their input on/to. If the windows service client finds that there exists any new mail(s) then it should download and filter the email body and push further for processing based on the user input in the email. You can host the input processing in the same windows service but it is not advisable to do so. The windows service can put the inputs in a special application directory or database from where your main appication can read the user inputs received in email and process them as needed.
You will be required to develop a high performance TCP/IP client for doing so. I advise you not to use the default .Net library due to performance issues, instead use one of the best availabel open source TCP/IP implementations for .Net like XF.Server from kodart. we have used this in our applications and achieved remarkably grear results.
Hope this helps..
Bose has a pretty great system where they embed a Queue and Ticket ID into the email itself.
My company has the traditional Case # on the subject line, but when CREATING a case, require a specific character string "New Case" "Tech Support Issue" on the subject line to get through the spam filters.
If the email doesn't match the create or update semantics, the autoresponder sends an email back to the recipient demonstrating how to properly send an email, or directs them to our forums or web support site.
It helps eliminate the spam issue, and yet is still accessible to a wide technical audience that is still heavily email dependent.
Spam is going to be a bit of a concern. However since you are initiating the conversation you can use the presence of your unique identifier (I prefer to use the subject line - "Trouble ticket: Unable to log into web...[artf123456]") to filter out spam. Be sure to check the filter on occasion since some folks mangle the subject when replying.
Email is a cesspool of bad standards and broken clients. You need to be prepared to accept almost anything as input. You will need to be very forgiving about what kinds of input are tolerated. Anything easy for you to program will likely be difficult for your users to use correctly. Consider the old mailing list programs that require you to issue commands in the subject line. Only hardcore nerds can use those effectively. And some of those trouble-ticket CRM things you mentioned have bizarre requirements, such as forcing the user to reply between two specific text markers in the text. That sort of thing is confusing to people.
You'll need to deal with email clients that send you formatted text instead of plain text. Some email clients still don't handle HTML properly (cough GMail) so your replies will also need to be designed appropriately. There are various ways in which photos might be "uploaded" via email as well, especially when mobile phones are involved. You will need to implement various hacks and heuristics to deal with these situations.
It's also entirely possible that you will get email that is valid but unusable by the email parsing library you are using. Whether or not this is important enough to roll your own will be a judgement call.
Finally, others have mentioned using specific email addresses to uniquely identify a "conversation". This is probably the easiest way to do this, as the content of the mail will often not survive a round trip to a client. Be prepared, however, to get mail to old IDs from old customers who, instead of opening a new ticket somehow, reply to an old ticket. Your application will probably need some way to push emails with an old ID into a new case, either manually or automatically. For a CRM system it's very likely that a user would reply to an old email even if you already sent him a new email with a new ID in it. As for whether you should use some.email.address+some.id#yourdomain.com or just some.id#yourdomain.com, I'd go with the latter because the plus-sign confuses some email clients. Make your IDs guids or something and have some way to validate them (such as a CRC or something) and you'll get less junk. Humans should never have to type in the GUIDs, just reply to them. The downside is spam filtering: a user's computer might view such email addresses as spam, and there wouldn't be an easy way to whitelist the addresses.
Which reminds me: sending email these days is full of pitfalls. There are many anti-spam technologies which make it extremely hard for you to send email to your customers. You will need to research all of these and you need to be careful, and do some testing, to ensure that you can reach the major email providers. A website like Campaign Monitor
can help you if you are sending email.
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In Cuba, web access is extremely censored, so I created a tool that allows more than 50,000 people to browse the Internet through email. Cubans send me an email with an URL in the subject line, and I email them back with the response. Read more at https://apretaste.com.
It was working like a charm, till the communist government of Cuba started blocking my emails. My solution was rotation.
I started with Amazon SES, and I was changing the domain each time it was blocked, but Amazon adds a header to all emails, and once they blocked the header no email from SES was able to reach Cuba any more. The same happened with Mailgun and others, they all add headers.
Currently I am creating Gmail accounts and sending via SMTP, but Google blocks me for no reason and only allows to send 100 emails a day per account. Also I can only create few emails using the same IP address/phone, so I was forced to use anonymous proxies and fake Chinese phones. Now I am fighting a war on two fronts.
An email can be blocked by three parameters: IP address, domain, and email address.
It will be terrific if I can set up my own Postfix server at a VPS that auto-rotates the IP address. Even better if I can simulate "gmail.com", to avoid purchasing a new domain every day.
All the intents to create what I call "the ultimate sender" just either reach the spam folder or add unwanted headers making it too easy to block. I feel exhausted. I hit a knowledge barrier here.
I know I am crossing to the dark side, but this is for a very good cause. Thousands count on this service as their only source of unbiased news, social network and to feel part of the 21st century.
Can you please help me implementing "the ultimate sender", or pointing to another solution that I may be missing?
I have a few suggestions for you.
The first one relies on The Onion Router also known as Tor.
Since you are crossing to the dark side, why not also take a look into the darknet?
Take a look at this list of Tor email providers. If you have your own email server that can be accessed through Tor, it becomes much harder for anybody to stop people from using this service. After all, Tor was developed to offer people uncensored access to the web.
You can read about Tor in detail here, it uses Onion Routing and this is how you would set up your server to use Tor.
Here is an example how you could use it:
The steps that involve the setup, receiving an URL request and sending back the reply are as follows:
Set up an email server.
Configure your email server to use Tor.
Publish the public service name. (e.g. "duskgytldkxiuqc6.onion")
Deploy a client that takes the service name and a URL, and let it send an email with a request to your server.
The client now waits for a reply.
You send a reply and the client receives it.
You can change your service name on a regular basis, but you need to make it accessible to those who will use this service.
Having an own email server means being able to control the email header.
Here is one example how you could make use of it:
Configure your email server so that it receives and recognizes
emails which contain the requested URLs.
Before you send a reply modify the email header so that it shows a random IP address and a random sender email address including a random domain name.
Send your reply.
Sending an email that way means that you cannot be replied back to. But since your reply already contains the requested information there is no need to.
I hope this helps.
Crowd source it.
Find a way that volunteers can send some emails for you. This is the only long term approach that I can think of. A simple web interface with mail to links would be be enough to get started although there are other potential problems with this approach too.
Because you are talking about low numbers of users, you could also use crowdsourcing to create the single email address per person approach. They can create an account on a specific set of email providers and give you the credentials. This would allow the single email per user approach or could be used to rotate through a large set of email accounts to send emails.
The simplest solution is perhaps to set up a local SMTP server on your own computer. You don't even need a server per se.
https://sourceforge.net/projects/winsmtpserver/
There are many other such applications. They are usually used to test SMTP functions during local development, but there is nothing against actually sending spam through them.
I know this would be quite a large task, but how about pairing the users with one or just a few emails so they always receive an email from that email.
I'd assume people wouldn't have more than 100 queries per day, if so they could start receiving them from a backup email
I'd imagine it would look less suspicious for them to appear to be in constant contact with one unique email rather than 50,000 being in contact with one
I know this would be a huge undertaking, but I feel like it solves your issue.
Since the users are willing to receive emails form you then your shouldn't be blocked.
When you mentioned you are getting block does it mean your mail is going in spam or is getting lost in between sending and receiving or it is getting bounced back??
My suggestion would be to setup your own mail server and follow as below:
-Get approx 25 or more ip to rotate. (IP is the most imp part which is tracked and is accountable for the reputation of your mail server)
Don't start sending emails in bulk from the word go it is better to gradullay increase the email volume so that mail server reputation nicely built
keep changing the format of the email often
encourage user to add yourself to there contact list
your best part is user are willing to receive emails from you and you would reply to revived email is the USP of yours but still i will recommend you to register for FBL so that you would know which user is reporting you as spam and you can remove him from your list and never send him email again.
using best practice to send emails like dkim, SPF, dmarc are also vital.
Hope my answer was of some help to you. If you need step by step guide to step up mail server let me know.
My friend, do you remember what made Hillary Clinton lose the last elections to Trump?
It was the "mail" affair. And what was it? People discovered she shared confidential information through a non-official, non-governmental email account (i.e., she used some Gmail, Yahoo or another of a kind). Until here, nothing new with direct relation to your matters. But there is an small particularity on this history, and this can put, maybe not a solution, but maybe a light on a new path you could follow: Clinton actually never sent those emails; the email account she used had the password shared and the communication between people (Clinton-someone) occurred only using the drafts of the account.
How? One side logs in and accesses the drafts folder. There he/she reads the last message and edits it, cutting and writing new data - then save the draft message. On the next turn, the other side of the communication line logs in and do the same. And so forth, so never really sending those messages, but instead just updating the drafts (this "Hillary" method does schooled people... Dilma Rousseff, impeached ex-president of Brazil, actually did this method down there in Brazil too).
So, maybe if you could establish a pact with your user that he/she doesn't delete the account's password, you could pass those information by this method - without "really" exchanging emails. Maybe a "parent" email account (some that could reset a lost password) could be useful too.
Alternative: aren't you able to contract a regular HTTP webserver? You could rely on FTP to publish data to your user, he/she asks for it and you publish a page with that content.
Salvi, have you tried something with Telnet? OK, we are talking here about a text-only environment, but if nothing more would rest in the future, this could be better than nothing. Maybe you could implement a podcast-like, or push-like service based on it. Look what people do with it with references to your walk on the dark side...
If in Windows, open your command prompt.
Type telnet and press Enter.
Type "o" without quotes and press Enter.
Type "towel.blinkenlights.nl" without the quotes and press Enter.
I am sending out transactional emails in my app and was reading up on best practices (for spam reasons obviously) and the following strikes me as odd.
I was expecting notification emails from Google, Facebook etc to have simple sender addresses like update#facebook.com/no-reply#plus.google.com etc.
But the actual addresses seem to be update+zj4o9ocoaz66#facebookmail.com, noreply-daa26fef#plus.google.com etc
Is there any reason, technical or otherwise, for not having a single/simple sender address when sending out transactional emails to all users?
While I can't speak to Facebook and Google specifically, the main reason for this is tracking and parsing of bounce notifications.
If you look at the headers you will see the 'Return-Path' is the same - no-reply+hash#example.org - this address is where mail servers should send automated bounces for NDR (non-delivery), such as 'inbox full' or 'nonexistent address', although some systems will use the 'From' as well, hence what you see.
The 'hash' part is often a structured piece of data that may help guide to particular clusters, determine the type of email, or identify recipients. You will often find ticketing systems use the same method to ensure your messages are directed to the same support agent if you reply.
While you could technically use the Message-ID header for this, that header tends to be a non-colliding 'random' hash rather than specifically structured data to assist routing without relying purely on lookup tables.
I need to be able to display ads on email forwarded through a server (preferably postfix) based on the demographic information of the recipient. Basically a message will arrive for someuser#fakedomain.com and be forwarded to realuser#theirdomain.com with a small advertisement at the bottom.
I would like to use postfix because it appears to be able to use mysql data for various tasks, which would be beneficial so that the system could be controlled by a web app that feeds the database.
I'd prefer to use OpenX for the ad server due to targetting channels (used to select ads based on demographic information), the ability to do text ads as well as email zones, and the ability to run it locally. Other ad servers that are better suited to this problem are acceptable, of course.
The core of the problem, as I see it, is being able to write something at the bottom of any given email message. Of course html messages make this even trickier, but I'd settle for having a solution that works for plain text and work up from there.
Commercial software is an option as well, but a few days of intermittent searching hasn't turned anything up.
Simply writing something to the bottom of the email message will fail miserably in a LOT of cases, particularly with HTML email encapsulated in a MIME multipart message (or anything else in a MIME multipart message) because anything after the last MIME section marker is explicitly supposed to be ignored by any MIME parser. If you want your app to work it needs to
determine if the target message is a MIME message other than TEXT/PLAIN
If it is not, append your text only ad at the end and you're done
if it is, determine if its multipart
if not, then you need to determine the content type of the whole message
If the content type is HTML then you can attempt to insert your ad HTML somewhere appropriate. This will be very hit or miss since you have no idea what the HTML layout will be like.
if the content type is anything OTHER than HTML (or maybe RTF), you're best off not touching the message.
If the message is multipart, determine the subtype
if its 'mixed', then you need to determine which part if any is the primary readable content, and then modify that portion as if it were the whole message based on the above rules
If its 'alternative' then you need to find ALL the readable portions and modify each of them in turn according to the above rules
Finally, and most importantly
Be prepared for the massive ill will you will receive from everyone who gets mail routed through your server.
Let me see... People sign up for your service, which I assume is free. They provide you their real email address and in return you provide them a different email address which they can use to e.g. subscribe to mailinglists and for other services. And maybe some spamfilter functionality? That sounds like a legit service to me, especially if you only provide the ads to the person who subscribed. I do wonder if you'd get many subscriptions, though, since many people can just as easy use a Google, Yahoo or Hotmail account for these purposes. So, what is the added value those subscribers will get?
Anyway, you would need to modify existing emails, which is a bit complex when they are HTML mails or if they're digitally signed. (Especially in the latter case, you would actually block the recipient from receiving those emails, since their email system would detect that the email has been tampered with. You might also be at risk of possible legal problems, although I don't think there's anything illegal as long as the recipient agrees with the terms of your service.
I'm working on an application that will allow management to send registered users (opt-in) broadcast emails at regular intervals, or based on various other criteria. In any case, I'm curious as to whether I should send a separate email to each recipient or bcc all of them on a single message. Currently the email list would be about 1500 recipients, but it should scale all the way up to at least 25k without problems.
Thoughts? Am I getting into a range that I need to worry about being put on spam lists?
Yes, I've had spam list problem with mailing lists of that size, managing email lists for non-profits.
One wants to take extra precautions: make sure your email has SPF records, write a script to send the emails in batches, paced out over time. Definitely send them one one at a time, not as bcc, as direct mail has a better chance of arriving. Make it very easy to unsubscribe. Include people's subscribed email in the message sent -- often people have email forwarded to another account and then try to unsubscribe that account and get frustrated.
Even so, don't be surprised if you have to change your IP at some point.
You are getting into that range. This is the point where I would look to get a third party to send the email on my behalf. Let them worry about being marked as spammers, supply the bandwidth, etc.
I recently built an application with those same criteria. We do the emailing in-house, and send one email to each recipient.
Do use domain keys signing or be sure to use SPF records for your domain. We didn't do that at first, and were blacklisted by a number of different ISPs. Fortunately, it is fairly easy to get them to unblock you. Most will include an online form you can fill out or an email address you can use in the server bounce message.
Don't try to implement the actual email sending yourself. That's a huge waste of time. Either outsource the entire process to one of the many reputable vendors out there (Many organizations I deal with use Constant Contact, and it works well), or run a garden-variety mailing list server (e.g. Mailman) in-house.
Either way, take efforts to make it very easy to unsubscribe (good vendors have that covered), to authenticate that messages are from your company, and to show that your company is not spamming. Real mailing list server software supports all of these goals, by adding proper headers that identify the source very clearly and making unsubscription easy. For instance, Gmail will now offer to send unsubscribe requests in response to mailing list messages marked as 'spam', as has AOL for a long time.
Definitely set up SPF and DKIM if you can manage it.
Finally, whatever you do, make sure you keep logs of your subscriptions, so that if someone does accuse you of spamming, you can defend yourself.
The task is mostly uninteresting on a strictly technical level. You should worry about what happens when a recipient thinks that your list's content is spam and starts (a) complaining or (b) flagging the message as spam with one or more anti-spam service providers. Something like this is bound to happen with a list of the size you describe.
If you are prepared and have the time handle such cases, go for it, at least for a start. (Changing your mail server's IP address as Devin Ceartas suggests won't be of much use by the way.)
If you want to build your own thing, I have two pieces of advice:
Unsubscribing has to be easy, no more than one or two clicks. Using Mailman or any other mailing list manager that was intended for discussion mailing lists is asking for trouble.
BCCing the same message to 1500 (or 25k) recipients may take some load off your mail server, but it has one serious disadvantage: You won't be able to use VERP in order to determine if all addresses that have once been subscribed to your list are still valid. (Large mail providers tend to classify messages as spam if there are delivery attempts to many invalid addresses.)
Our clients sometimes don't get the emails that we send out. It's a BIG loss. How do I assure that they receive the emails so that if it's not received in the other end, the program can resend it or do something about it.
None of the suggestions above will work 100% of the time. Many email clients will (rightly so) refuse to load foreign images, negating the usefulness of "web bugs". They will also refuse (or be unable to) return Outlook-style "receipts". And many mail servers either deliberately (to curb spam) or mistakenly (due to misconfiguration) won't return bounce messages. Or possibly an over-aggressive spam filter ate your message, so it arrived but was never seen by the end user. Plus there is the little matter of mail taking hours or days to reach the end user or bounce, and how do you correlate these late notifications or bounces with the mail you sent 4 days ago?
So basically, you can catch some but not all, no matter what you do. I'd say that any design that relies on being able to know with certainty whether the end user got your mail is fatally flawed.
One thing that you can do is set up a bounceback address that receives any mail that is undeliverable. Use the bounceback address as the From address -- you may want a different one for Reply-To so that replies get directed properly.
Check the bounceback mailbox daily and contact customers to get updated email addresses for the ones that fail. You may be able to automate a couple of retries to failed addresses before resorting to the manual contact in case the failure is only intermittent.
This would take some code outside your application that scans the mailbox and keeps some state information about the number of contacts, etc. and attempts the resend.
Depending on how you generate the mails, you might be able to make this process easier: generate a unique bounce address for every single email you send out. You could use bounces+1234#example.com, for example.
Many SMTP servers will allow you to use the part after the + as a parameter to an external script, etc.
The problem is that many (broken) SMTP servers don't return enough info with a bounce to identify the original message -- sometimes, when there are forwardings involved, you don't even get back the original addressee...
With the above trick you can reliably correlate outgoing messages with incoming bounces.
There is no standard way to know whether the email reached the destination. Many email clients support different types of receipts though. You can use any of those if you want.
There are some ways to know when the user actually read the email.
There are many techniques like adding an image to your email that is to be fetched from your web server. When the user reads the email, the request for the image comes to your server and you can capture the event.
The problem is that there is no way to know that the mail did not reach the destination.
I worked on a bulk email system in a previous life. Deliverability was one of our major issues. The most common cause of undelivered emails is a spam filter.
Here are the steps we took to ensure the highest delivery rates:
We used Return Path to test emails for that spam-like smell.
If you send a lot of emails, you need to make sure your SMTP server is not blacklisted.
Remind your users to add your FROM address to their "safe senders" list.
Use a system that collects bouncebacks and use them to scrub your mailing list. This will also help keep you off the blacklists.
If the emails are critical, consider sending them return-receipt-requested. This will not really guarantee anything, but it might give you some metrics on actual deliverability.
There's not really a good way to determine if the email actually arrives in their inbox, you can only confirm that you sent it. Attach a receipt that lets you know when they open it perhaps?
Microsoft Outlook provides similar functionality, however it is based on the email client. I'm not sure if other clients, like Thunderbird, support this.
However, there is nothing in the protocols that specify receipts.
One option that may work: send a link to a generate web page and monitor that page for hits. This provides its own issues however: confidentiality, etc.