e-mails getting rejected

DougLass · 16 Mar 2023, 10:49 AM

I'm using Sender as a mailserver. My e-mails are getting Junked by many, including Microsoft (MSN, Outlook, Office 365). My SPF and DKIM are all verified, and look great. My IP is (judging from mxtoolbox.com), perfectly clean with regard to spam blacklisting. These e-mails are very benign, and have been sent via other mailservers with no issue. They don't LOOK like spam. So what the #$%^&*() is going on???

I entered my Sender IP into the Office 365 Anti-Spam IP Delist Portal, and I get back "The request to delist IP address xxx.xx.x.xxx has been denied." No reason given. I'm suspecting that this IP, while now blacklist-free, has had some serious problems in the past. So what are my options? BTW, I tried escalating the request, and I pretty much got back the same thing.

TenFour · 16 Mar 2023, 09:47 PM

Obviously, one option is to use a different mailing server. I've had decent luck with Mailerlite and Constant Contact. Does Server require you to scrub your mailing list to make sure you are sending to valid email addresses? Are you using your own list, or have you purchased lists? Do your emails have a clear and legitimate one-click unsubscribe link? Is your email very image heavy? Have you tried sending a very simple, mostly text email? What does your score look like at https://www.mail-tester.com/

DougLass · 16 Mar 2023, 10:00 PM

Yes, I used to use MailChimp, and had no problems with them, but with their free subscription, they no longer allow mail scheduling. That's a deal breaker for me. Sender free subscription does, and has a smarter user interface. But yes, dumping Sender and paying for service is always an option.

My e-mail lists are all valid, mostly industrial and federal. Sender imposes an unsubscribe link. Just one image - and that's for a modest header (again, that worked fine with MailChimp) I've tried mail-tester.com, and get 8.5/10. "We found 1 images without alt attribute in your message body" - duh, who cares? Also, ha ha, my personal Google Fiber IP that I sent it from is listed in two blacklists. That's not relevant to Sender. Is mail-tester just looking for spammy e-mail or is it actually assessing the transmission? If the latter, then I'd have to send it from Sender, in which case it would be reporting back to Sender, and not me.

The question here is what the !@#$%^& is going on? At least the Office 365 Anti-Spam IP Delist Portalcould do is tell me WHY they don't like it.

TenFour · 16 Mar 2023, 10:04 PM

Mail-tester requires you to go back to the page where you copied the address and then check your score there. It tests you against blacklists, for spf, dkim, etc. Just send one of your recent emails that was blocked to the mail-tester address using Sender and then go to the page where you picked up the mail-tester address. Just tested one of my Gmail accounts and it scored 9/10. I would say anything under a seven would have delivery problems.

EDIT: I should add that Microsoft is a thorny problem in my experience. Every single day I have to check my spam folders at work because Microsoft puts legitimate emails in there even if they are contacts, have sent emails to me for years, and even when they are internal emails from other people in our organization! It is one reason why I vastly prefer Gmail for my own personal use, and if I was starting a new small company I would avoid Microsoft email. For example, we just ordered some equipment from PayPal who our company has had an account with for probably at least a decade, and we receive nearly daily emails from them for one purpose or another. I just checked my Junk folder and there were several emails there from PayPal concerning this order. It is a huge pain.

DougLass · 16 Mar 2023, 10:14 PM

OK, I just did mail-tester via my Sender IP, and I got 10/10. I did get a "Your message does not contain a List-Unsubscribe header", but there IS an unsubscribe footer. Besides, mail-tester regards that only as a suggested improvement. I should add that it is my understanding that many large corporations and federal agencies use Microsoft Outlook, and as a result, are beholden to it's perfidity. And that's right. I get messages from these folks telling me that even internal messages to them get dumped in their Junk folders. Now, why am I having problems with Sender, and never did so with MailChimp? As far as I can tell, the only difference is the sender IP.

BTW, I very much appreciate the pointer to mail-tester.com!

TenFour · 16 Mar 2023, 10:20 PM

Yes, I have had the same problem even with personal emails sent to companies using Microsoft for their email. Unfortunately, it is by far the most popular service for business and government in the USA, so we must deal with it. One guess would be that if Sender is cheap or free it has been abused by spammers and phishers, and Microsoft has some sort of special treatment for it. I would imagine they would be much more hands off with MailChimp or they would be blocking just too many emails.

DougLass · 16 Mar 2023, 11:41 PM

Yes, it could be that Microsoft just doesn't like Sender! Now, lots of listserve providers have free options, including MailChimp, so if folks want to spam, they have a lot of free options. If Microsoft has it in for Sender, it's not clear why. When I started with Sender they DID give me an IP that was blacklisted, but I protested, and they replaced it. The one I have now is squeaky clean.

I should add that, amusingly, the Microsoft Office 365 Anti-Spam IP Delist Portal is at https://sender.office.com/, which might suggest that Sender has something to do with it. But they don't.

malcontent · 17 Mar 2023, 03:23 AM

Twilio SendGrid

https://sendgrid.com/

I have no experience with them but they have a free option. I don't know if they would meet your needs.

DougLass · 17 Mar 2023, 04:19 AM

As I said, lots of listserve e-mailers have free options. It would seem that the straightforward solution is just finding out why the hell Microsoft is blocking my e-mails. I'm not asking for an exception. I just want a REASON that I can work to fix. It's simply nuts that there doesn't seem to be a way to get that information out of Microsoft. I have no idea who else they're blocking. Sort of like if you get a ticket from the police but, nope, they won't tell you why.

Is there really no way to get that info out of Microsoft??

BTW, the Sendgrid free option allows 100 e-mails per day. I'm doing twice that many. Most other listserve e-mailers allow such large numbers for free.

DougLass · 22 Mar 2023, 08:51 PM

OK, so out of the blue yesterday, I get a Comcast DMARC Report Generator report for my IP that Sender has assigned to me. I don't believe I ever asked for this. Strange XML file. If I interpret it correctly, I "pass" everything EXCEPT

<row>
<source_ip>xxx.x.xxx.xxx</source_ip>
<count>3</count>
<policy_evaluated>
<disposition>none</disposition>
<dkim>pass</dkim>
<spf>fail</spf>
</policy_evaluated>
</row>

where xxx.x.xxx.xxxis my IP address. I am led to believe that this DMARC report generator doesn't like my SPF. Sender and Hostgator (my domain supplier) have validated my SPF. So what the @#$%^&* does this mean?

TenFour · 22 Mar 2023, 09:23 PM

Can you check your DNS yourself to make sure the SPF record is correct and there is only one? One of my domain registrars keeps adding back their own SPF record to my DNS for some reason, resulting in two records. Also, I have made typing errors when entering the SPF. What does mail-tester say about SPF?

DougLass · 22 Mar 2023, 09:26 PM

As I said, both Sender and Hostgator have checked my SPF, and it looks fine, they say. What does Comcast know that they don't? My SPF record has a Hostgator IP and my Sender IP. That's it. It's exactly one record. And yes,my SPF didn't originally have a Hostgator IP, but Hostgator inserted that.

TenFour · 22 Mar 2023, 09:28 PM

MX Toolbox is also useful for checking SPF records: https://mxtoolbox.com/spf.aspx

DougLass · 22 Mar 2023, 09:36 PM

The domain is, let's say, xxx.net.
The e-mail is, let's say, me@xxx.net.

My SPF for xxx.net is
v=spf1 +mx +a +ip4:108.167.133.30 +include:sendersrv.com ~all

My SPF for me@xxx.net is
v=spf1 +mx +a +a:sendersrv.com +ip4:108.167.133.30 +ip4:xxx.x.xxx.xxx ~all

108.167.133.30 is the Hostgator IP. Hostgator inserted this themselves. xxx.x.xxx.xx is my Sender IP (which I am reluctant to reveal).

https://mxtoolbox.com/spf.aspx likes them both, but gives a "soft fail" on ~all, presumably because it just thinks it's too lenient.

TenFour · 22 Mar 2023, 09:44 PM

Not sure what Sender says about SPF, but this Constant Contact help page is pretty good at explaining how things work when using a mailing service to send email for your own domain. https://knowledgebase.constantcontac...ess?lang=en_US

However, you must have only one SPF record: https://dmarcly.com/blog/can-i-have-...s-on-my-domain

16 Mar 2023, 10:49 AM	#1
DougLass Member Join Date: May 2014 Posts: 56	e-mails getting rejected I'm using Sender as a mailserver. My e-mails are getting Junked by many, including Microsoft (MSN, Outlook, Office 365). My SPF and DKIM are all verified, and look great. My IP is (judging from mxtoolbox.com), perfectly clean with regard to spam blacklisting. These e-mails are very benign, and have been sent via other mailservers with no issue. They don't LOOK like spam. So what the #$%^&*() is going on??? I entered my Sender IP into the Office 365 Anti-Spam IP Delist Portal, and I get back "The request to delist IP address xxx.xx.x.xxx has been denied." No reason given. I'm suspecting that this IP, while now blacklist-free, has had some serious problems in the past. So what are my options? BTW, I tried escalating the request, and I pretty much got back the same thing.

16 Mar 2023, 10:00 PM	#3
DougLass Member Join Date: May 2014 Posts: 56	Yes, I used to use MailChimp, and had no problems with them, but with their free subscription, they no longer allow mail scheduling. That's a deal breaker for me. Sender free subscription does, and has a smarter user interface. But yes, dumping Sender and paying for service is always an option. My e-mail lists are all valid, mostly industrial and federal. Sender imposes an unsubscribe link. Just one image - and that's for a modest header (again, that worked fine with MailChimp) I've tried mail-tester.com, and get 8.5/10. "We found 1 images without alt attribute in your message body" - duh, who cares? Also, ha ha, my personal Google Fiber IP that I sent it from is listed in two blacklists. That's not relevant to Sender. Is mail-tester just looking for spammy e-mail or is it actually assessing the transmission? If the latter, then I'd have to send it from Sender, in which case it would be reporting back to Sender, and not me. The question here is what the !@#$%^& is going on? At least the Office 365 Anti-Spam IP Delist Portalcould do is tell me WHY they don't like it. Last edited by DougLass : 16 Mar 2023 at 10:07 PM.

16 Mar 2023, 10:04 PM	#4
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,722	Mail-tester requires you to go back to the page where you copied the address and then check your score there. It tests you against blacklists, for spf, dkim, etc. Just send one of your recent emails that was blocked to the mail-tester address using Sender and then go to the page where you picked up the mail-tester address. Just tested one of my Gmail accounts and it scored 9/10. I would say anything under a seven would have delivery problems. EDIT: I should add that Microsoft is a thorny problem in my experience. Every single day I have to check my spam folders at work because Microsoft puts legitimate emails in there even if they are contacts, have sent emails to me for years, and even when they are internal emails from other people in our organization! It is one reason why I vastly prefer Gmail for my own personal use, and if I was starting a new small company I would avoid Microsoft email. For example, we just ordered some equipment from PayPal who our company has had an account with for probably at least a decade, and we receive nearly daily emails from them for one purpose or another. I just checked my Junk folder and there were several emails there from PayPal concerning this order. It is a huge pain. Last edited by TenFour : 16 Mar 2023 at 10:17 PM.

16 Mar 2023, 11:41 PM	#7
DougLass Member Join Date: May 2014 Posts: 56	Yes, it could be that Microsoft just doesn't like Sender! Now, lots of listserve providers have free options, including MailChimp, so if folks want to spam, they have a lot of free options. If Microsoft has it in for Sender, it's not clear why. When I started with Sender they DID give me an IP that was blacklisted, but I protested, and they replaced it. The one I have now is squeaky clean. I should add that, amusingly, the Microsoft Office 365 Anti-Spam IP Delist Portal is at https://sender.office.com/, which might suggest that Sender has something to do with it. But they don't. Last edited by DougLass : 16 Mar 2023 at 11:51 PM.

17 Mar 2023, 04:19 AM	#9
DougLass Member Join Date: May 2014 Posts: 56	As I said, lots of listserve e-mailers have free options. It would seem that the straightforward solution is just finding out why the hell Microsoft is blocking my e-mails. I'm not asking for an exception. I just want a REASON that I can work to fix. It's simply nuts that there doesn't seem to be a way to get that information out of Microsoft. I have no idea who else they're blocking. Sort of like if you get a ticket from the police but, nope, they won't tell you why. Is there really no way to get that info out of Microsoft?? BTW, the Sendgrid free option allows 100 e-mails per day. I'm doing twice that many. Most other listserve e-mailers allow such large numbers for free. Last edited by DougLass : 17 Mar 2023 at 04:26 AM.

16 Mar 2023, 09:47 PM	#2
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,722	Obviously, one option is to use a different mailing server. I've had decent luck with Mailerlite and Constant Contact. Does Server require you to scrub your mailing list to make sure you are sending to valid email addresses? Are you using your own list, or have you purchased lists? Do your emails have a clear and legitimate one-click unsubscribe link? Is your email very image heavy? Have you tried sending a very simple, mostly text email? What does your score look like at https://www.mail-tester.com/

16 Mar 2023, 10:14 PM	#5
DougLass Member Join Date: May 2014 Posts: 56	OK, I just did mail-tester via my Sender IP, and I got 10/10. I did get a "Your message does not contain a List-Unsubscribe header", but there IS an unsubscribe footer. Besides, mail-tester regards that only as a suggested improvement. I should add that it is my understanding that many large corporations and federal agencies use Microsoft Outlook, and as a result, are beholden to it's perfidity. And that's right. I get messages from these folks telling me that even internal messages to them get dumped in their Junk folders. Now, why am I having problems with Sender, and never did so with MailChimp? As far as I can tell, the only difference is the sender IP. BTW, I very much appreciate the pointer to mail-tester.com!

16 Mar 2023, 10:20 PM	#6
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,722	Yes, I have had the same problem even with personal emails sent to companies using Microsoft for their email. Unfortunately, it is by far the most popular service for business and government in the USA, so we must deal with it. One guess would be that if Sender is cheap or free it has been abused by spammers and phishers, and Microsoft has some sort of special treatment for it. I would imagine they would be much more hands off with MailChimp or they would be blocking just too many emails.

17 Mar 2023, 03:23 AM	#8
malcontent Essential Contributor Join Date: Oct 2008 Posts: 275	Twilio SendGrid https://sendgrid.com/ I have no experience with them but they have a free option. I don't know if they would meet your needs.

22 Mar 2023, 08:51 PM	#10
DougLass Member Join Date: May 2014 Posts: 56	OK, so out of the blue yesterday, I get a Comcast DMARC Report Generator report for my IP that Sender has assigned to me. I don't believe I ever asked for this. Strange XML file. If I interpret it correctly, I "pass" everything EXCEPT <row> <source_ip>xxx.x.xxx.xxx</source_ip> <count>3</count> <policy_evaluated> <disposition>none</disposition> <dkim>pass</dkim> <spf>fail</spf> </policy_evaluated> </row> where xxx.x.xxx.xxxis my IP address. I am led to believe that this DMARC report generator doesn't like my SPF. Sender and Hostgator (my domain supplier) have validated my SPF. So what the @#$%^&* does this mean?

22 Mar 2023, 09:23 PM	#11
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,722	Can you check your DNS yourself to make sure the SPF record is correct and there is only one? One of my domain registrars keeps adding back their own SPF record to my DNS for some reason, resulting in two records. Also, I have made typing errors when entering the SPF. What does mail-tester say about SPF?

22 Mar 2023, 09:26 PM	#12
DougLass Member Join Date: May 2014 Posts: 56	As I said, both Sender and Hostgator have checked my SPF, and it looks fine, they say. What does Comcast know that they don't? My SPF record has a Hostgator IP and my Sender IP. That's it. It's exactly one record. And yes,my SPF didn't originally have a Hostgator IP, but Hostgator inserted that.

22 Mar 2023, 09:28 PM	#13
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,722	MX Toolbox is also useful for checking SPF records: https://mxtoolbox.com/spf.aspx

22 Mar 2023, 09:36 PM	#14
DougLass Member Join Date: May 2014 Posts: 56	The domain is, let's say, xxx.net. The e-mail is, let's say, me@xxx.net. My SPF for xxx.net is v=spf1 +mx +a +ip4:108.167.133.30 +include:sendersrv.com ~all My SPF for me@xxx.net is v=spf1 +mx +a +a:sendersrv.com +ip4:108.167.133.30 +ip4:xxx.x.xxx.xxx ~all 108.167.133.30 is the Hostgator IP. Hostgator inserted this themselves. xxx.x.xxx.xx is my Sender IP (which I am reluctant to reveal). https://mxtoolbox.com/spf.aspx likes them both, but gives a "soft fail" on ~all, presumably because it just thinks it's too lenient.

22 Mar 2023, 09:44 PM	#15
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,722	Not sure what Sender says about SPF, but this Constant Contact help page is pretty good at explaining how things work when using a mailing service to send email for your own domain. https://knowledgebase.constantcontac...ess?lang=en_US However, you must have only one SPF record: https://dmarcly.com/blog/can-i-have-...s-on-my-domain