Listervs have been migrated to a new server redux

(Update:  be sure to look at Richard Schafer’s comment below, about how to whitelist in Microsoft’s system.)

Hello to the members of the various listservs hosted by Oppedahl Patent Law Firm LLC.   Five days ago I migrated the listservs to a new server.  For many members of the listservs, it looks like this migration has gone largely unnoticed after a few test postings of yesterday and today.  But for some members, this migration has not worked out well, because of the behavior of their email service provider, which is called “Outlook” from Microsoft. 

The executive summary is that Microsoft is wrongly treating our emails as if they were spam, and listserv members who use Microsoft as their email service provider will need to ask Microsoft to stop doing this.

Here are the details.

Many times in the past few days I have received inquiries from members of the listserves that we host, asking about their listserv membership.  Here are examples of the inquiries:

• • the member was receiving listserv postings quite regularly before about October 5, 2023, but has received few or no listserv postings after about October 5, 2023, or
  • the member has tried to do a “password reminder” on the member information page, and the email message that provides a reminder of the password does not arrive.

What happens next is that I log in at the listserv server to see what is going on.   I go to a system called “track delivery”.  I plug in the email address of the member who made inquiry to me.  The delivery tracker generates a report that shows the most recent 25 times that the listserv server sent, or tried to send, email to that email address.  What I see in most of these cases is a report along the  lines of what you can see in the table below.  (In this particular table I have redacted and anonymized some text for privacy.)  The situation is that an email service provider “outlook” from Microsoft is pretending to be “busy” and suggests that our listserv server should “try again later”.

This pretence by “outlook” of being “busy” and this asking our listserv server to “try again later” is, of course, a big problem for the listserv member because the listserv member is failing to receive the desired email messages.   It is also a big problem for me because I then get a big scolding from my hosting provider (Namecheap) which tells me that I am making a lot of trouble for the Namecheap company, because I am sending suspected spam emails, and they know this because “outlook” is doing this “busy” and “try again later” behavior.

This happens because “outlook” is wrongly assuming that email messages from our listserv server (at its new IP address) are spam.

There are several important things to appreciate in all of this.  First, if only Microsoft were to be at least a tiny bit discerning in its analysis of inbound emails (which it apparently is not), Microsoft would see that the “from” email domain of “@oppedahl-lists.com” was known to be non-spam before November 5 (emitted from IP address 162.255.116.157) and so it ought to continue be considered non-spam after November 5 (emitted from IP address 66.29.132.148).  But it seems that when the emails arrive from this new IP address 66.29.132.148, Microsoft starts all over again with some (incorrect) presumption that the emails must be spam.

You might wonder whether our hosting provider (Namecheap) gave us a tainted IP address.  You might wonder whether, when our hosting provider assigned this new IP address 66.29.132.148 to our new server, did our hosting provider give us some IP adddress that had already been tainted in some way by whoever was using that IP address in the past?  And the answer is no.  You can plug this new IP address into systems that look at all of the commonly used RBL (realtime black-hole) systems and they all say that the IP address is “clean”.  (There is one odd exception to this, an RBL system called “UCEPROTECTL3” which I have blogged about here.  The UCEProtect system does not disapprove of any past behavior from the specific IP address 66.29.132.148, but does disapprove of recent behavior from some other IP addresses that are numerically “nearby” to that IP address.)

I should emphasize that for many years now, our firm has been “doing everything right” about sending emails.  Among the things that we have been “doing right” for many years is that our outbound email servers use properly configured DKIM (Wikipedia article) and SPF (Wikipedia article) and PTR (Wikipedia article) records to prove to any skeptical email service provider (such as Microsoft) that our outbound emails are legitimate.  But that is not good enough for Microsoft in the past five days for our new IP address 66.29.132.148.  Nor is it good enough for Microsoft that our new IP address is “clean” on every RBL system (except the UCEPROTECTL3 system).

Indeed a person can do tests at Microsoft’s own Microsoft Remote Connectivity Analyzer.  The Microsoft Remote Connectivity Analyzer gives a clean bill of health to both of our email senders (63.250.38.181 for oppedahl.com and 66.29.132.148 for oppedahl-lists.com).  But that’s not good enough for Microsoft.  Microsoft’s inbound email server continues to pretend to be “”busy” and continues to tell us to “try again later”.

What can the listserv member do about this?  The main thing is for the listserv member to do whatever they need to do with their email service provider to  “whitelist” our IP addresses (66.29.132.148 and 63.250.38.181) and to “whitelist” our email domains (“oppedahl-lists.com” and “oppedahl.com”).  The listserv member may wish to complain directly to Microsoft about its behavior.

The sending email addresses include:

• • copyright@oppedahl-lists.com
  • designs@oppedahl-lists.com
  • e-trademarks@oppedahl-lists.com
  • efs-il@oppedahl-lists.com
  • efs-web@oppedahl-lists.com
  • designs@oppedahl-lists.com
  • madrid@oppedahl-lists.com
  • pair@oppedahl-lists.com
  • patentcenter@oppedahl-lists.com
  • patentpractice@oppedahl-lists.com
  • pct@oppedahl-lists.com
  • st26@oppedahl-lists.com

Here is a typical report showing the discourteous behavior by Microsoft:

Event	From Address	Sent Time	Recipient	Result
warning	pair-bounces@oppedahl-lists.com	11/10/23 02:56 AM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [BN8NAM04FT017.eop-nam12.prod.protection.outlook.com 2023-11-10T11:35:14.496Z 09CBDEEC46A050E3]
warning	pair-bounces@oppedahl-lists.com	11/10/23 02:56 AM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [MW2NAM04FT093.eop-nam12.prod.protection.outlook.com 2023-11-10T10:59:17.130Z 09CBE1BE8F0B0654]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 09:34 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [DM6NAM04FT007.eop-nam12.prod.protection.outlook.com 2023-11-10T11:06:22.804Z 09CBE1050E9FC7F8]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 09:34 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [MW2NAM04FT079.eop-nam12.prod.protection.outlook.com 2023-11-10T10:12:58.342Z 09CBDB32A6D26164]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 09:34 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [DM6NAM04FT093.eop-nam12.prod.protection.outlook.com 2023-11-10T09:27:48.969Z 09CBDD12206D002A]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 09:34 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [DM6NAM04FT074.eop-nam12.prod.protection.outlook.com 2023-11-10T08:16:14.819Z 09CBDCD5CCA8F231]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 09:34 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [MW2NAM04FT080.eop-nam12.prod.protection.outlook.com 2023-11-10T07:36:53.288Z 09CBDB574E5E40DB]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 09:34 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [BN8NAM04FT012.eop-nam12.prod.protection.outlook.com 2023-11-10T06:14:53.097Z 09CBE14D2E3C29DE]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 09:34 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [DM6NAM04FT100.eop-nam12.prod.protection.outlook.com 2023-11-10T05:34:26.693Z 09CBE145486EEBFC]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 08:56 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [MW2NAM04FT031.eop-nam12.prod.protection.outlook.com 2023-11-10T11:23:27.407Z 09CBE0E6BBDB2454]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 08:56 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [MW2NAM04FT082.eop-nam12.prod.protection.outlook.com 2023-11-10T09:40:57.956Z 09CBE10D16875A91]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 08:56 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [MW2NAM04FT003.eop-nam12.prod.protection.outlook.com 2023-11-10T08:20:19.976Z 09CBD9DCB8C29033]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 08:56 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [BN8NAM04FT003.eop-nam12.prod.protection.outlook.com 2023-11-10T07:24:00.933Z 09CBE1BAD25037BB]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 08:56 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [DM6NAM04FT093.eop-nam12.prod.protection.outlook.com 2023-11-10T06:34:03.841Z 09CBDD12205AB0A4]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 08:56 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [MW2NAM04FT080.eop-nam12.prod.protection.outlook.com 2023-11-10T05:18:41.955Z 09CBDB574E506B75]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 08:56 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [MW2NAM04FT099.eop-nam12.prod.protection.outlook.com 2023-11-10T04:57:43.264Z 09CBE102B8E21A35]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 06:45 PM	g****e@j*******elaw.com	retry time not reached for any host for ‘j*******elaw.com’
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 06:45 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [DM6NAM04FT089.eop-nam12.prod.protection.outlook.com 2023-11-10T10:05:55.054Z 09CBDD1E4BC8E9BC]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 06:45 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [BN8NAM04FT047.eop-nam12.prod.protection.outlook.com 2023-11-10T09:37:26.242Z 09CBE14C7B3119E5]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 06:45 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [DM6NAM04FT058.eop-nam12.prod.protection.outlook.com 2023-11-10T08:25:00.182Z 09CBE16095537859]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 06:45 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [BN8NAM04FT007.eop-nam12.prod.protection.outlook.com 2023-11-10T07:15:59.876Z 09CBE15BC1ADAABE]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 06:45 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [MW2NAM04FT070.eop-nam12.prod.protection.outlook.com 2023-11-10T06:04:51.101Z 09CBE051396B3150]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 06:45 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [DM6NAM04FT021.eop-nam12.prod.protection.outlook.com 2023-11-10T05:19:09.381Z 09CBE020CBD35F26]
warning	patentcenter-bounces@oppedahl-lists.com	11/09/23 06:45 PM	g****e@j*******elaw.com	SMTP error from remote mail server after end of data: 451 4.7.500 Server busy. Please try again later from [66.29.132.148]. (S77719) [DM6NAM04FT004.eop-nam12.prod.protection.outlook.com 2023-11-10T04:28:07.116Z 09CBE0F9AA6E3122]

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