SendGrid SMTP API: Multiple e-mails to the same recipient - email

I have a web app that uses SendGrid's X-SMTP functionality to construct a single e-mail that is then merged and forwarded to a list of recipients specified in the X-SMTPAPI header.
Documentation here: http://sendgrid.com/docs/API_Reference/SMTP_API/
I am using MVC.NET and sending the e-mail using a MailMessage object via smtp.sendgrid.net
Everything seems to be working fine as far as merging values from the header and sending out the e-mails is concerned.
However I have noticed that if I specify the same e-mail address multiple times in the "to" list, only a single e-mail is sent out (or at least I just receive the one).
Has anybody had the same experience? Anybody know of a way to get around this issue?
Thanks in advance!

SendGrid's servers will de-dupe the To array. The only way to get around this is to split duplicates into separate SMTP messages, or to change the addresses so they are not duplicates (you could use plus addressing, e.g. person#example.com and person+foo#example.com).

Related

Forcing new thread in Gmail

We send an automated email whenever someone signs up for our app.
The subject is always the same for every user.
Let's say the subject is 'Welcome'.
The problem is that whenever someone replies, it always end up in a single giant thread in gmail.
So the emails from various users are interleaved with each other, which makes it very difficult to manage.
What we want is a single thread per user (i.e per recipient email address) so that we can keep the conversation with each person separate.
I'm aware that gmail has its own way of grouping messages into thread based on the subject line by default.
However, we noticed that some support tools (such as Zendesk) have somehow find a way to keep each email separate even though the same subject line is used. They seem to have a work around.
What I mean is that we have received multiple emails from the Zendesk email sender with the same subject and somehow they end up in multiple threads in our gmail.
They don't seem to use a uniquely generated email either. The from and reply-to address is simply support#domain.com
How do they do it?
We experimented with the 'Message-ID' and 'In-Reply-To' SMTP headers but were unsuccessful.
Sending emails with different Message-ID still end up in the same thread.
See example of a Zendesk email received to my gmail address below:
Since I can't post in the comment, will add to the answer here. Sample headers in an email I received from Zendesk. Note that they use the support email address + the ID of the support ticket as the 'Reply-To' address.

Can I Use Postmark to Create Threaded Replies?

Like many web apps, we use Postmark to send all notifications for server side events. Many of our events are grouped and related by something simple and logical (think multiple replies to the same issue, like in GitHub).
Right now, every email sent for these related events is it's own email thread. My question is: how do I send these emails so that related ones get pushed into the same thread?
I'm not sure if this is something at the Postmark level (like include a previous message ID) or if this is something I do with SMTP (like I should format my subject better and inline previous responses), so that's why I'm seeking guidance. Also, every Google search about: "Postmark email threads" returns concerns over the thread safety of the Ruby Gem.
For more information, the app is written in PHP and right now we are znarkus/postmark-php for sending emails and jjaffeux/postmark-inbound-php for parsing inbound ones. However, I am more than willing to add any extra packages if they help me in my quest.
Thanks in advance!
You can add a few SMTP headers with the original Message-ID that most clients use to link together replies. If the original email had a Message-ID header of <123#mail.example.com> the new email you send out should keep the subject line the same and add headers of:
In-Reply-To: <123#mail.example.com>
References: <123#mail.example.com>
And that should inform clients that the two emails should be threaded.
Edit:
The value for these headers should be the SMTP Message-ID header, which is slightly confusing because it is a separate concept from the Postmark MessageID value, which is just a UUID for the email.
The SMTP Message-ID header is always in the form an email address, because that's how it's supposed to be formed, but doesn't have to be related to the from address.

Routed google domain emails

i have an idea about system where users respond to website's messages using the emails they received.
Is it even possible to have multiple imaginary emails with hash in the e-mail's name field(f.e., 1h2149g0as1gasd9123#mysite.com ) and those all imaginary e-mails just forward content to messaging#mysite.com e-mail. And afterwards we are able to parse the contents and know for which conversation the message was sent.
The emails are hosted in Google service. Could not find any information about this in internet.
Such option would be excellent, because there would be no need of including the identificator in e-mail's content which might be deleted if no quoted text is in replied e-mail.
I'm open to any other suggestions that would fit in this situation.
When using Google's service, you can add tags after the e-mail address using a +. For example...
test#domain.com
test+12345#domain.com
test+wuishw78#domain.com
will all go through to test#domain.com, and you can then look at the address.
Note this is not supported by all e-mail systems, so while this works on Google's hosted e-mail, it may not work on others.

For non-customized bulk email, is it better to use the BCC field, or generate a separate email with To header for each recipient?

I'm generating a bulk mailing each day for users who want to receive the daily deals. I can either send a separate physical email with each user specified on their own unique To header, or I can send one email with all the users on the BCC line.
Obviously if I ever want to create user specific content I will need to customize the emails per user and send them individually, but if I don't want customized email right now, should I just send out the single email with everyone on BCC? Any reason to NOT do that.
Edit: I'm using a third party as my gateway that specializes in delivery with CAN-SPAM compliance, etc.. not trying to do this off my own mail server...
Update: I guess I'm really also looking for some metrics here. Is there a difference in open rates of BCC'ed email vs To field email? What about spam filtering rules that might pre-classify based on the BCC field?
No reason I can think off for NOT doing it. Using BCC is the polite way to send bulk emails.
In this case, it turns out that the correct answer was neither. The gateway provided a custom header API that allowed me to specify all the recipients in a secondary "To" field. The API then handled the blind delivery of the emails, and also did variable substitution for me so I didn't have to transmit all the duplicate content multiple times. The API then handled doing "best practices delivery of the email".

Sending emails to multiple recipients - best practices

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.