Send email attachments, and getting platforms to trust them

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chevrolux

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#225813 6-Dec-2017 19:51

So we have moved our monthly recurring invoices to a new platform we are running in-house on our CRM.

It's as simple as it gets, invoice gets generated, and then emailed to client attached as a PDF.

It works extremely well and the vast majority and receiving their bills as normal. However, we are getting a higher than expected amount of people saying they haven't received an invoice in reply to our reminder notices that get sent out at 28-days ("just a reminder your invoice xxxxx is due today..."). But they are obviously getting the reminder notice no problem. The only parallel I can draw from this is that the reminder notice doesn't have an attachment, but the initial mail out does.

Mail is being sent via SMTP2GO. We have the correct SPF and DKIM records set up for the sending domain - i hate to think how many of those "verify" services I have tested them against.

What more can we do to ensure delivery?

I do wonder if we perhaps need to think about adopting the same method as Spark or "click here to view your bill" link in the email. But frankly that will require FAR too much work in the back end for now and it's just easy to resend invoices to clients.

irpegg

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#1914075 6-Dec-2017 20:01

Although it may seem basic http://mail-tester.com is actually overly informative.

If nothing stands out from that, try looking at mail logs. One issue i've been seeing lately is DMARC bounces going to google address etc.

modcar

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#1914101 6-Dec-2017 20:15

Does the pdf have the correct header information?

I experienced something similar when the application wasn't generating the pdf correctly so mail scanners would block it

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chevrolux

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#1914110 6-Dec-2017 20:37

modcar: Does the pdf have the correct header information?

I experienced something similar when the application wasn't generating the pdf correctly so mail scanners would block it

Ooo interesting. I have no idea!

I can quite easily write that in to the PDF generation though. What headers does it need?

@timbee - thanks will run it through that too and see what I find out.

chevrolux

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#1914113 6-Dec-2017 20:47

Right so mail-tester.com gave me a 10/10 - guess i must have done something right (or more likely SMTP2GO are doing everything right)/

It points out I don't have a DMARC record on the domain - have added that now, just hope it won't cause any unwanted issues. SPF and DKIM do check out fine, as expected, so should be all good there.

It tells me the message could be improved ...but only by adding an unsubscribe link, so not so helpful there.

modcar

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#1914144 6-Dec-2017 22:18

chevrolux:
Right so mail-tester.com gave me a 10/10 - guess i must have done something right (or more likely SMTP2GO are doing everything right)/

It points out I don't have a DMARC record on the domain - have added that now, just hope it won't cause any unwanted issues. SPF and DKIM do check out fine, as expected, so should be all good there.

It tells me the message could be improved ...but only by adding an unsubscribe link, so not so helpful there.

I can't remember exactly, but open a 'normal' pdf in notepad and look at the first line.

When I ran I to this problem, the application was putting a character in front of what was supposed to be there.

Dynamite Design & Hosting
www.dynamite.net.nz

modcar

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#1914146 6-Dec-2017 22:19

Whoops, quoted wrong reply!

Dynamite Design & Hosting
www.dynamite.net.nz

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MadEngineer

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#1914162 6-Dec-2017 22:38

Could I get you to email me a sample to my work address? PM me if so.

You're not on Atlantis anymore, Duncan Idaho.

chevrolux

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#1914355 7-Dec-2017 08:47

MadEngineer: Could I get you to email me a sample to my work address? PM me if so.

Sure! PM sent

MadEngineer

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#1915253 8-Dec-2017 12:24

Email came through, can't see any issues.

Definitely need to check send logs and if the delivery was successful, provide this as proof of delivery to the recipients and have them follow up with their support as to why they're not receiving your mail.

You're not on Atlantis anymore, Duncan Idaho.

chevrolux

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#1916037 10-Dec-2017 16:17

Awesome.

Yep I think I will just keep a better note of who is complaining and who runs their mail services.

I'm confident we're doing what we should to minimise mail going to junk. If people can't allow mail from us or decide to use paranoid ISP supplied services that's not my problem.

vulcannz

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#1916047 10-Dec-2017 16:49

Some places - particular those with poor email solutions - are blocking attachments in an attempt to deal with malware/ransomware.

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chevrolux

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#1916180 10-Dec-2017 18:58

vulcannz:

Some places - particular those with poor email solutions - are blocking attachments in an attempt to deal with malware/ransomware.

Yep just going back through the last handful. Majority are xtra addresses. We deal with small businesses so heaps still have these ISP supplied ones. I remember seeing a thread on here about SMX being super paranoid on attachments at one stage.

If complaints about not receiving invoices get to me again, my response will be a quote of moving the customer to Office 365.

martyyn

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#1916871 11-Dec-2017 17:17

I've had to deal with this a fair amount over the last 12 months for one of my clients. He sends out quotes, invoices and attachments with two internet based CRM's and there is always someone calling to say they haven't received an email, or he gets an error with a generic 500 bounce error.

I started off knowing relatively little about it, probably still only know very little, but every single time it came down to their client having some poxy email solution which involved some free overseas hosting, super cheap domain hosting and forwarding the email to another address (typically an ISP address).

Never ceases to amaze me how many businesses have such awful set ups.

chewster

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#1919942 15-Dec-2017 00:21

Is the email address you're sending from monitored, or are bounce-backs getting back to you via a Return-Path header address? Could be possible your SMTP providers send IP is on an SMX internal IP blacklist, monitor mail logs when sending to SMX as they normally give useful error responses.

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