email is being seen as junk/spam by hotmail/live/outlook accounts

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andreapapo
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email is being seen as junk/spam by hotmail/live/outlook accounts

Post by andreapapo » 2015-03-11 13:21

Hello,

The emails that I send are seen as junk/spam by hotmail/live/outlook accounts.

I install hmailserver 5.6.1 (database sql 2012 r2) on Windows 2012 r2 vps (ip 151.80.117.122) as web/mail server.

At the moment i've just 3 domain (mine and 2 customer) but would like to transfer other domains from shared hosting .

I'm in trouble because when i send mail to Windows account (Hotmail, live, Outlook) every mail go straight to junk folder. I've never sent newsletter mailing list, automatic response and similar, i'm talking about usual email with some text inside.

I've a static ip of course, I setup reverse dns ptr record (thru ISP) that matches my mail server host name, IP is not on any public blacklists, Setup MX, DKIM, SPF, DMARC. Sending test mail at http://www.mail-tester.com/ obtain 10/10 points.

Mail are absolutely normal, not like a spam. I join snds and jmrp microsoft programs because it was suggested by microsoft support.

I contact Microsoft thorough eform https://support.msn.com/eform.aspx?prod ... ct=eformts but they give me this response:
We have reviewed your IP(s) (151.80.117.122 ) and determined that messages are being filtered (i.e. sent to the Junk folder) based on the recommendations of the SmartScreen® Filter.
Email filtering is based on many factors, but primarily it's due to mail content and recipient interaction with that mail. Because of the proprietary nature of SmartScreen® and because SmartScreen® Filter technology is always adapting and learning more about what is and isn't unwanted mail, it is not possible for us to offer specific advice about improving your mail content. However, in general SmartScreen® Filter evaluates specific words or characteristics from each e-mail message and weights them, based on their likelihood to indicate that a message is unwanted or legitimate mail.


I've tried to send many different emails to many different microsoft account and from every email account of my server but the problem is the same. I also tried to change email clients (webmail, outlook, thnderbird) and also a simply message sent by telnet.

I can send to gmail and yahoo without problems (at beginning there was similar problem but after contacting gmail and yahho support everything is ok) I read similar post but not found a clear solution and spent many days to try resolve. Do you have any suggestion?

I know microsoft has our proprietary technology as antispam filter but it is possible to make it happy with my emails .. @ softkey.it ?

Please help me

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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by jimimaseye » 2015-03-11 13:45

Good old MS. Probably no help.

What happens if you send a blank innocuous email?

Something like:

"Hi Ted

Do you have any response for my earlier email?

Cheers"

And what do the headers of the marked spam email say? Do they give you a clue? ("x-outlook-Failed SPF" or something)

EDIT: interesting. Ive just done the same test and my emails do the same. My headers are

Code: Select all

x-store-info: 4r51+eLowCe79NzwdU2kR3P+ctWZsO+J
Authentication-Results: hotmail.com; spf=pass (sender IP is 186.14.221.220) smtp.mailfrom=sales@mycompany.com; dkim=none header.d=mycompany.com; x-hmca=pass header.id=sales@mycompany.com
X-SID-PRA: sales@mycompany.com
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n

Hmmmm....
Last edited by jimimaseye on 2015-03-11 14:01, edited 1 time in total.
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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by andreapapo » 2015-03-11 13:58

thanks for reply..

I don't see anything helpful in the header, here the text:

x-store-info:4r51+eLowCe79NzwdU2kRyU+pBy2R9QCSLYaJ5Qj56/cTRAx3RJldnXJfvu3b1JOY8ONTX6+dNVGrTeQZjbsEXO5uifz1Fnm1lXq1exwu3ygVJnIHnVqOVyIajUGqs5sLyKZLPcy9nM=
Authentication-Results: hotmail.com; spf=pass (sender IP is 151.80.117.122; identity alignment result is pass and alignment mode is relaxed) smtp.mailfrom=ele.andrea@softkey.it..; dkim=pass (identity alignment result is pass and alignment mode is relaxed) header.d=softkey.it; x-hmca=pass header.id=ele.andrea@softkey.it..
X-SID-PRA: ele.andrea@softkey.it..
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD02
X-Message-Info: 11chDOWqoTlqNZlbq2agccGDUffnODDSj0EiIL2V9LipukYh2aVQSNYuCrXy35ArqYi4isaZPX6N5iZz0x5YkBMrDwfLP/rfCIl2D2tkdyXMckcbvnlv12R3lJokQYXDJwIUlAA1A6rQH6jTmpoo4q1SSofpNrMxLqQFmCz14oYtHCsXFeK8lh7EVIHdq/EzHms09hqrHsBTJim4uSa2k9OMkhrAEHjT
Received: from mail.softkey.it ([151.80.117.122]) by SNT004-MC4F31.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.22751);
Wed, 11 Mar 2015 04:53:40 -0700
dkim-signature: v=1; a=rsa-sha1; d=softkey.it; s=mail;
c=relaxed/relaxed; q=dns/txt; h=From:Subject:Date:Message-ID:To:MIME-Version:Content-Type;
bh=kaXhHDkmd8kKd2o4MNZaYKDJWZw=;
b=KV640JOwUMjAmDJ1ATtM/VqFeBNyezKKMlYyVe6Gn4B6lp80JYrqCeuugH9eFGCQzOaUXYBJl4Dv4EkWN7zMFtPnDbh25CY4/XX+yD/FvR7qsQyTIp//daBFZxc5ihIbQokFRMdrh7gbAaTHnJUHB21XCK2IrKbowYuVlrodZ50=
Received: from softkey.it (SERVER12 [127.0.0.1])
by mail.softkey.it with ESMTPA
; Wed, 11 Mar 2015 12:54:00 +0100
MIME-Version: 1.0
X-Mailer: MailBee.NET 6.0.2.220
X-Priority: 3 (Normal)
From: "Andrea Eleuteri" <ele.andrea@softkey.it>
To: a.eleuteri@outlook.it..
Subject: response for my mail
Date: Wed, 11 Mar 2015 12:54:00 +0100
X-Originating-IP: 80.207.147.163
Message-ID: <2.c54b6c80addb02c7920a@SERVER12>
Content-Type: multipart/alternative;
boundary="----=_NextPart_000_B681_C1FC21E6.D40E2673"
Return-Path: ele.andrea@softkey.it..
X-OriginalArrivalTime: 11 Mar 2015 11:53:40.0224 (UTC) FILETIME=[0411E800:01D05BF2]

------=_NextPart_000_B681_C1FC21E6.D40E2673
Content-Type: text/plain;
charset="utf-8"
Content-Transfer-Encoding: quoted-printable

Hi Ted

Do you have any response for my earlier email?

Cheers

------=_NextPart_000_B681_C1FC21E6.D40E2673
Content-Type: text/html;
charset="utf-8"
Content-Transfer-Encoding: quoted-printable

<html><body>Hi Ted<br><br>Do you have any response for my earlier email?<br=
><br>Cheers<br></body></html>
------=_NextPart_000_B681_C1FC21E6.D40E2673--

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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by jimimaseye » 2015-03-11 14:04

Does this help: https://mail.live.com/mail/troubleshooting.aspx
IPs not previously used to send email typically don't have any reputation built up in our systems. As a result, emails from new IPs are more likely to experience deliverability issues. Once the IP has built a reputation for not sending spam, Outlook.com will typically allow for a better email delivery experience.
New IPs that are added for domains that are authenticated under existing SPF records typically experience the added benefit of inheriting some of the domain's sending reputation. If the domain has a good sending reputation new IPs may experience a faster ramp up time. A new IP can expect to be fully ramped within a couple of weeks or sooner depending on volume, list accuracy and as long as their junk email complaint rates are kept at a minimum.
Sounds like there is squat you can do.
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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by andreapapo » 2015-03-11 14:33

I've already read this interesting article, more times.

Maybe is a problem of ip/domain reputation but it's very strange because domain has 10 year and ip is relative new :2 months (the article say that it need max 2 weeks).

Dou you think can be a problem of interaction between hmailserver (or its particolar configuration) and Microsoft server ?

I've a quite default configuration of hmailserver.

Were you able to send without go to junk folder ?

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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by jimimaseye » 2015-03-11 14:48

No I wasnt, Imine also went to Junk on my test earlier.

IT says 'relatively new' and you say you have been there for 2 months. But have you been actively sending to homtail accounts of 2 months? Im guessing they determine the frequency over a period of time too.

In any case, I dont think there is anything you can do about it. Nothing. SMTP is SMTP (as long as you are applying to the RFC regs). And it seems you are. Once it has been sent for delivery the receiving server doesnt know what flavour of SMTP server it is coming from so wouldnt care about your HMS. It only cares about your IP and its reputation (and of course the content and format of the messages).

If yo have regular hotmail receivers, you will have to tell them to WHITELIST your address.
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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by andreapapo » 2015-03-11 15:41

yes i send email regularly to Microsoft account since 2 months.

I've already whitelisted my Microsoft account but I create a couple of new Microsoft account for testing purpose because all email sent to new contact go to their junk folder.
It's a real problem because we can reply to email of potential new customer and they can not see mail in their inbox.

I appreciate your help, at the end I think like you, but hope to find something to do for having a quickly resolution.

Just to know.. also your server as a relative new ip ? What do you think about your email going to junk folder ?

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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by jimimaseye » 2015-03-11 15:54

Our server has been around for 2 or 3 years BUT, as I say, it doesnt matter if you never send an email to hotmail/outlook account. Only when they receive emails from us will they know about us and check on us. So for all I know (but doubt it) that test this morning could have been the first hotmail account we have ever sent to. (99.998% of our emails are to business/private domain email addresses)

It is a mystery as to why/how MS employ this method if it is seeming so problematic to users (just google and you will see). But in the end there is nothing we can do.

God bless Microsoft.
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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by andreapapo » 2015-03-11 16:25

Many Thanks! 8)

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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by jimimaseye » 2016-03-15 17:23

More detailed reading and explanation from Microsfot. Taken from https://mail.live.com/mail/troubleshooting.aspx

This section provides troubleshooting information for senders who are having trouble reaching Outlook.com users by email. If you are an Outlook.com user looking for support with your account, please visit our end user support page.
If you are experiencing problems delivering email to Outlook.com please first ensure that you are following all of the requirements found on our Policies and Guidelines page.

Common Problems

Are you managing your IP and domain's sending reputation?

Microsoft's SmartScreen® technology is designed to provide anti-spam filtering innovations for Outlook.com as well as other Microsoft products like Exchange Server, Microsoft Office Outlook and Windows Live Mail. We also leverage SPF , an email authentication technology protocol that helps address the problem of spoofing and phishing by verifying that the domain sending the email is authorized to do so. SmartScreen® email filters are influenced by a number of factors related to the sending IP, domain, authentication, list accuracy, complaint rates, content and more. Of these, one of the principal factors in driving down a sender's reputation and deliverability is their junk email complaint rate.

Are you sending email from new IPs?

IPs not previously used to send email typically don't have any reputation built up in our systems. As a result, emails from new IPs are more likely to experience deliverability issues. Once the IP has built a reputation for not sending spam, Outlook.com will typically allow for a better email delivery experience.
New IPs that are added for domains that are authenticated under existing SPF records typically experience the added benefit of inheriting some of the domain's sending reputation. If the domain has a good sending reputation new IPs may experience a faster ramp up time. A new IP can expect to be fully ramped within a couple of weeks or sooner depending on volume, list accuracy and as long as their junk email complaint rates are kept at a minimum.
Note: don't forget to update your Junk Email Reporting Program (JMRP) account with the new IPs. To update or set up a JMRP account, click here.

Are you running Anti-Virus software?


Some of the deliverability issues are the result of sender-based software configurations. If you are running anti-virus software on your firewall or SMTP server, check for the setting "Internet Email Auto Protect" or "Internet Email Protection." If this setting is enabled, disable it and try sending a test message to our servers again.
If you are currently running Symantec AntiVirus Corporate Edition 9.x or 10.x on your server, please review this article from Symantec Support.

Confirm that your DNS is set-up correctly


Try connecting to mail.hotmail.com via port 25. If you are unable to connect, then attempt to telnet over port 25 directly to our email servers (MTAs). You can find the current list of our MTAs by querying "nslookup –q=mx hotmail.com" from a command prompt (this should work in a variety of Operating Systems). Currently, the addresses for these servers are mx1.hotmail.com, mx2.hotmail.com, mx3.hotmail.com and mx4.hotmail.com. If that doesn't work, try connecting directly to the IPs. If you are able to connect directly to the IP and not mail.hotmail.com, then it is likely there is an issue with your DNS server.
Occasionally, some of the IPs in our MX record may be out of service. If you are connecting to one of these IPs your connection may timeout. Make sure you test all of our published IPs. You may also configure your outbound email server to do a round-robin DNS lookup for Outlook.com.

Are you advertising yourself as a non-routable IP?

We may not accept email from senders who fail a reverse-DNS lookup. In some cases legitimate senders advertise themselves incorrectly as a non-internet routable IP when attempting to open a connection to Outlook.com. IP addresses that are reserved for private (non-routable) networking are 192.168.0.0/16, 10.0.0.0/8, and 172.16.0.0/11 (or 192.168.0.0 - 192.168.255.255, 10.0.0.0 - 10.255.255.255, 172.16.0.0 - 172.31.255.255).

Sender services, tools, and issue submission

We have developed some tools and services which will give you more information about how our users are rating your email. These services have been tailored for senders and for ISPs. To learn more about the Sender and ISP Services, go here.
If your email complies with our policies and guidelines and you are still experiencing email delivery problems that are not addressed in the FAQ below, click here to contact support.
Note: Deliverability issues submitted using this form should only be related to the Outlook.com system, including any address @msn.com, @Outlook.com, @hotmail.com, or @live.com. We will do our best to help you troubleshoot your issue. However, submitting this information does not guarantee that any message you send to users of the Outlook.com services will be delivered.

Are you blocked for namespace mining?

Senders must not use namespace mining techniques against Outlook.com inbound email servers. This is the practice of verifying email addresses without sending (or attempting to send) emails to those addresses. This method is commonly used by malicious senders to generate lists of valid e-mail addresses that they can send spam, phishing emails or malware. Microsoft does not allow this behavior and takes action on IPs that engage in it. If any of your sending IPs is blocked for namespace mining, please check that your machines or email sending accounts are not compromised by an attacker who may be using your servers to harvest email addresses, and ensure that any method you use to validate email addresses does not use namespace mining techniques.

Frequently Asked Questions

Why does the email that I send to Outlook.com users sometimes look different from what they receive?

Avoid using scripting languages as they may be removed from your message. Many email messages now contain HTML code similar to that found in a Web page. This often helps with formatting and design. Outlook.com now analyzes and processes HTML content to remove HTML code that may be unsafe for your computer. This change is part of Microsoft's overall Trustworthy Computing Initiative and was made to further reduce the risk of malicious HTML content reaching our users.

How can I prevent my messages from being marked as from an "unknown sender" in the Outlook.com interface?

One way to ensure that your messages aren't marked as being from an "unknown sender" is to join Return Path's Certification program, a third-party accreditation and reputation service that provides Outlook.com with a list of responsible senders. Alternatively, if an Outlook.com user adds your domain or email address to their "contacts" or their "safe-senders list" they will no longer see this notification. In addition, senders who are on the Return Path Certification list or on a user's "safe sender's" list typically experience links and images within their messages enabled by default.

Does Outlook.com operate an "allow list" that I can get on?

No. An "allow list" is essentially a "free pass" which allows emails from certain senders to bypass junk email filters and other precautions. Outlook.com evaluates all inbound email for malicious content. You can find out more about our filtering processes here. We do, however, partner with Return Path, Inc. who helps ensure the legitimacy of certain senders via their Return Path Certification program. This program allows Outlook.com to exercise greater assurance about mail from certified senders in good standing. You can learn more about the Return Path Certification program here.

How do I avoid having my messages marked as potentially dangerous?

To help prevent your messages from being identified as possibly fraudulent:
  • Always use valid, reputable URLs. Make sure it's clear where the recipient will be taken and whether the destination is a valid website.
    Use the standard URL format. Avoid using IP addresses in the URL.
    Whenever possible, publish your Sender Policy Framework (SPF) records.
    Do not link to known phishing sites.
Why did I receive a "550 command rejected due to Sender ID validation failure." SMTP Non-Delivery Report (NDR) when I attempt to send mail to Outlook.com users?

Outlook.com will not allow delivery of email sent from a domain where the Sender ID record was configured by the domain owner to NOT allow ANY IP to send mail from that domain. Sender ID allows a domain owner to protect domains that aren't intended for sending email in order to help protect their domain from being spoofed. This can be done by publishing a simple TXT record in DNS like the following example (note: the organization would replace example.com with their own domain and or sub-domain name):
example.com IN TXT "v=spf1 -all"
If the domain is repurposed to send mail, the administrator of the DNS record should update the Sender ID record to include the IP address(s) that are authorized to send mail from that domain. Note that updates to your Sender ID record can take up to 48 hours to propagate through the Internet, so it's a good idea to wait 48 hours after making a change to your record before you initiate any new email activities. In addition, Microsoft strongly recommends that you conduct email testing prior to sending live communications to your users/customers.

SMTP Error Codes

SMTP Error Code - Explanation
421 RP-001 The mail server IP connecting to Outlook.com server has exceeded the rate limit allowed. Reason for rate limitation is related to IP/domain reputation. If you are not an email/network admin please contact your Email/Internet Service Provider for help.

421 RP-002 The mail server IP connecting to Outlook.com server has exceeded the rate limit allowed on this connection. Reason for rate limitation is related to IP/domain reputation. If you are not an email/network admin please contact your Email/Internet Service Provider for help.

421 RP-003 The mail server IP connecting to Outlook.com server has exceeded the connection limit allowed. Reason for limitation is related to IP/domain reputation. If you are not an email/network admin please contact your Email/Internet Service Provider for help.

550 SC-001 Mail rejected by Outlook.com for policy reasons. Reasons for rejection may be related to content with spam-like characteristics or IP/domain reputation. If you are not an email/network admin please contact your Email/Internet Service Provider for help.

550 SC-002 Mail rejected by Outlook.com for policy reasons. The mail server IP connecting to Outlook.com has exhibited namespace mining behavior. If you are not an email/network admin please contact your Email/Internet Service Provider for help.

550 SC-003 Mail rejected by Outlook.com for policy reasons. Your IP address appears to be an open proxy/relay. If you are not an email/network admin please contact your Email/Internet Service Provider for help.

550 SC-004 Mail rejected by Outlook.com for policy reasons. A block has been placed against your IP address because we have received complaints concerning mail coming from that IP address. We recommend enrolling in our Junk Email Reporting Program (JMRP), a free program intended to help senders remove unwanted recipients from their email list. If you are not an email/network admin please contact your Email/Internet Service Provider for help.

550 DY-001 Mail rejected by Outlook.com for policy reasons. We generally do not accept email from dynamic IP's as they are not typically used to deliver unauthenticated SMTP email to an Internet mail server. If you are not an email/network admin please contact your Email/Internet Service Provider for help. http://www.spamhaus.org maintains lists of dynamic and residential IP addresses.

550 DY-002 Mail rejected by Outlook.com for policy reasons. The likely cause is a compromised or virus infected server/personal computer. If you are not an email/network admin please contact your Email/Internet Service Provider for help.

550 OU-001 Mail rejected by Outlook.com for policy reasons. If you are not an email/network admin please contact your Email/Internet Service Provider for help. For more information about this block and to request removal please go to: http://www.spamhaus.org.

550 OU-002 Mail rejected by Outlook.com for policy reasons. Reasons for rejection may be related to content with spam-like characteristics or IP/domain reputation. If you are not an email/network admin please contact your Email/Internet Service Provider for help.




So there you have it! :mrgreen:
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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by percepts » 2016-03-15 18:29

go into your softkey.it DNS and change your SPF TXT record to following:

softkey.it TXT v=spf1 ip4:151.80.117.122 mx a -all

NOTE: that is -all and NOT ~all

If your users domains are sending mail using your server at mail.softkey.it then set each of their DNS to use spf record which says:

theirdomain.com TXT v=spf1 include:softkey.it -all

Let us know if that solves the problem.

AND

you have a weird looking TXT record at softkey.it which says:

softkey.it TXT 1|www.softkey.it

do you know what its for and is it meant to be there? if not then remove it.

AND

don't set a priority when you send email. Use normal priority if you must use it but better off without it.

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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by Furball Zen » 2016-06-10 16:12

I know this is a bit older, but has it been resolved? Its possible that because you are in Europe you are being flagged. It sucks, but it may be as simple as that. I had to create a rule to block many EU addresses including .it because so much spam either comes from those TLD's, or are spoofed as such.

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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by mkaliyannan » 2016-09-15 23:26

Hi all, Anyone had a luck ?? I am also having same issue... mail tester gives me 10/10. Gmail, office 365,yahoo and others are no issues. only sucks with hotmail,outlook,live. Please let me know if anyone got fixed..

No IP blacklist
DMARC is good
SPF is good
DKIM is good
PTR records is good.
SMTP banner is good.

Still batling...

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Re: email is being seen as junk/spam by hotmail/live/outlook accounts

Post by jimimaseye » 2016-09-16 00:18

The answer is above in the thread.

more info: viewtopic.php?f=21&t=29763
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