MS Outlook Professional Plus 2019, POP3 Fail

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G4ELI
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MS Outlook Professional Plus 2019, POP3 Fail

Post by G4ELI » 2020-11-27 16:59

Hi All,

Installed hMailServer, integrated with phpBB and works superbly.

My problem is getting MS Outlook Professional Plus 2019 configured. My PC is 192.168.5.163, the hMailServer is 192.168.5.146, Firewall currently off for this test (makes no difference).

I've attached screenshots, what on earth can the problem be?

Code: Select all

"DEBUG"	11812	"2020-11-27 14:56:39.750"	"Creating session 107"
"TCPIP"	11812	"2020-11-27 14:56:39.750"	"TCP - 192.168.5.163 connected to 192.168.5.146:110."
"DEBUG"	11812	"2020-11-27 14:56:39.766"	"TCP connection started for session 106"
"POP3D"	11812	106	"2020-11-27 14:56:39.766"	"192.168.5.163"	"SENT: +OK Hello Camper"
"DEBUG"	11812	"2020-11-27 14:56:39.766"	"The read operation failed. Bytes transferred: 0 Remote IP: 192.168.5.163, Session: 106, Code: 2, Message: End of file"
"DEBUG"	11812	"2020-11-27 14:56:39.766"	"Ending session 106"
TIA, Simon G4ELI
Attachments
Logfile.jpg
hMailServer logfile
Outlook.jpg
Outlook Connection Attempt

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johang
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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by johang » 2020-11-27 17:32

G4ELI wrote:
2020-11-27 16:59
Hi All,

Installed hMailServer, integrated with phpBB and works superbly.

My problem is getting MS Outlook Professional Plus 2019 configured. My PC is 192.168.5.163, the hMailServer is 192.168.5.146, Firewall currently off for this test (makes no difference).

I've attached screenshots, what on earth can the problem be?

Code: Select all

"DEBUG"	11812	"2020-11-27 14:56:39.750"	"Creating session 107"
"TCPIP"	11812	"2020-11-27 14:56:39.750"	"TCP - 192.168.5.163 connected to 192.168.5.146:110."
"DEBUG"	11812	"2020-11-27 14:56:39.766"	"TCP connection started for session 106"
"POP3D"	11812	106	"2020-11-27 14:56:39.766"	"192.168.5.163"	"SENT: +OK Hello Camper"
"DEBUG"	11812	"2020-11-27 14:56:39.766"	"The read operation failed. Bytes transferred: 0 Remote IP: 192.168.5.163, Session: 106, Code: 2, Message: End of file"
"DEBUG"	11812	"2020-11-27 14:56:39.766"	"Ending session 106"
TIA, Simon G4ELI
but you can access through pop3 with same settings via other client ? its just a problem with outlook ??
___________________________________________________________end of the line

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by G4ELI » 2020-11-27 18:48

Hi,

Same problem with the standard Windows mail app. My Windows Firewall is off, Malwarebytes is off.

FWIW I can connect Outlook to a mail server on Google using IMAP.

This seriously smells of firewall / anti-virus but where ?

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by G4ELI » 2020-11-27 18:53

Fixed!

Disabled SSL/TLS requirement for my local address.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by SorenR » 2020-11-27 19:38

G4ELI wrote:
2020-11-27 18:53
Fixed!

Disabled SSL/TLS requirement for my local address.
Is this the time I should point out that standard POP3 port 110 SHOULD NOT be encryptet and that POP3 port 995 SHOULD be encryptet?

You are free to do whatever you like BUT standards are made to be followed and separate the amateur from the professional...

"This is the way"
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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by G4ELI » 2020-11-27 19:49

I added another entry in IP Ranges, this had Require SSL/TLS for authentication enabled by default, that's what caught me out.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by SorenR » 2020-11-27 20:34

G4ELI wrote:
2020-11-27 19:49
I added another entry in IP Ranges, this had Require SSL/TLS for authentication enabled by default, that's what caught me out.
Hmm... That seems to be inexpedient when encryption is managed in the "TCP/IP ports" section.
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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by jim.bus » 2020-11-27 21:16

SorenR wrote:
2020-11-27 19:38
G4ELI wrote:
2020-11-27 18:53
Fixed!

Disabled SSL/TLS requirement for my local address.
Is this the time I should point out that standard POP3 port 110 SHOULD NOT be encryptet and that POP3 port 995 SHOULD be encryptet?

You are free to do whatever you like BUT standards are made to be followed and separate the amateur from the professional...

"This is the way"
SorenR,

I agree with your point about the Standards for Ports. Your statement fits with what I have known for years about encryption on the various Standard Email Ports. While I have made my own requirements for encryption on my own hMailServer since I am the only user that connects with a client, the Standards are as you say which make me in disagreement with the 'Latest' hMailServer Help Documentation which states the Standard Encryption settings for the Standard Ports.

See this link.

https://www.hmailserver.com/documentati ... to_install

I believe the information in this hMailServer link is incorrectly stated and should be changed back to what the correct Port Encryption settings are. As you say, for instance, Port 110 is supposed to be unencrypted. But hMailServer Help Documentation indicates it should be Encrypted which is incorrect. I do not know if there are updated RFCs which may have changed this though. I have seen references to the RFCs which indicate that certain Ports such as I believe it was Port 465 were not actually considered an email Port but for legacy purposes was still recognized for use as an email Port.

By the way it looks like you are a 'The Mandalorian' fan. 'This is the way'.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by SorenR » 2020-11-27 22:11

I have been configuring ISP's, ITSP's and IP services all over the world for the past 30 years. Trust me, there are standards for ALL ports exposed to The Internet.

https://www.iana.org/assignments/servic ... search=995
jim.bus wrote:
2020-11-27 21:16

By the way it looks like you are a 'The Mandalorian' fan. 'This is the way'.
Oh yes... Just learned 'the kid' is actually called Groku ... And ... Ahsoka Tano is HOT! :mrgreen:

Tidbit... Yoda placed Ahsoka Tano as Anakin Skywalker's Padawan during the Clonewars...
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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by jim.bus » 2020-11-27 23:46

SorenR wrote:
2020-11-27 22:11

Oh yes... Just learned 'the kid' is actually called Groku ... And ... Ahsoka Tano is HOT! :mrgreen:

Tidbit... Yoda placed Ahsoka Tano as Anakin Skywalker's Padawan during the Clonewars...
I've mostly watched the live action Star Wars stuff. I do like 'The Mandalorian'. But I thought last week with the exposure of 'The Mandalorian's' mouth to eat that he may have slightly violated his Vow to never show his face. I wished they hadn't gotten rid of IG though. He was a great character. Haven't looked at today's episode yet. I finally go a Roku Device so I could watch it on my 60" TV. I was getting tired of having to watch it on only my 27" Computer Monitor. My stupid Samsung 60" TV is only 5 or 6 years old but it can't get the Disney+ Streaming Channel. However, Roku will work on it and it can get Disney+.

If you're a Science Fiction fan as I am, this is only a book series but I like the series by Edward E. Smith referred to as 'The Lensmen Series'. I consider it to be the best series in Science Fiction written where there are very few inconsistencies from one book to the other. It is a series of 6 books (don't be fooled into believing the 7th book is really in the series - It only takes place in the same 'Lensmen Universe'). This series has had influence in much of today's Science Fiction. The Green Lantern Corps (Comic Books) can be seen to have been influenced by The Lensmen Series. Two of the Green Lanterns was named after characters from The Lensmen series and the whole Corps could be likened to the Lensmen. So, if you like Science Fiction books as well and are not familiar with this series, I highly suggest you check it out. There are even other books written by other authors with permission from the Smith Estate that are supposed to be additional Lensmen books but I really didn't like them compared to the original series.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by SorenR » 2020-11-28 00:45

jim.bus wrote:
2020-11-27 23:46
SorenR wrote:
2020-11-27 22:11

Oh yes... Just learned 'the kid' is actually called Groku ... And ... Ahsoka Tano is HOT! :mrgreen:

Tidbit... Yoda placed Ahsoka Tano as Anakin Skywalker's Padawan during the Clonewars...
I've mostly watched the live action Star Wars stuff. I do like 'The Mandalorian'. But I thought last week with the exposure of 'The Mandalorian's' mouth to eat that he may have slightly violated his Vow to never show his face. I wished they hadn't gotten rid of IG though. He was a great character. Haven't looked at today's episode yet. I finally go a Roku Device so I could watch it on my 60" TV. I was getting tired of having to watch it on only my 27" Computer Monitor. My stupid Samsung 60" TV is only 5 or 6 years old but it can't get the Disney+ Streaming Channel. However, Roku will work on it and it can get Disney+.

If you're a Science Fiction fan as I am, this is only a book series but I like the series by Edward E. Smith referred to as 'The Lensmen Series'. I consider it to be the best series in Science Fiction written where there are very few inconsistencies from one book to the other. It is a series of 6 books (don't be fooled into believing the 7th book is really in the series - It only takes place in the same 'Lensmen Universe'). This series has had influence in much of today's Science Fiction. The Green Lantern Corps (Comic Books) can be seen to have been influenced by The Lensmen Series. Two of the Green Lanterns was named after characters from The Lensmen series and the whole Corps could be likened to the Lensmen. So, if you like Science Fiction books as well and are not familiar with this series, I highly suggest you check it out. There are even other books written by other authors with permission from the Smith Estate that are supposed to be additional Lensmen books but I really didn't like them compared to the original series.
I have a Xiaomi Mi TV Box S 4K connected to our Pioneer 42" plasma ... Android ... Can even connect to my surveillance cams ;-)

Here it's my son that keep track of everything - I never seem to have time to read a book anymore. I believe I'm more of a Battlestar Galactica, Star Trek and Superman (Christopher Reeve) generation ;-)
Having said that ... We (family) have seen all the MCU movies since The Incredible Hulk (2008) together. 8)
SørenR.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by jim.bus » 2020-11-28 02:45

SorenR wrote:
2020-11-28 00:45

Here it's my son that keep track of everything - I never seem to have time to read a book anymore. I believe I'm more of a Battlestar Galactica, Star Trek and Superman (Christopher Reeve) generation ;-)
Having said that ... We (family) have seen all the MCU movies since The Incredible Hulk (2008) together. 8)
I actually prefer Star Trek to Star Wars though I do like Star Wars and I absolutely liked Daisy Ridley as Rey. I really like seeing little slips of a girl kicking the shit out of evil guys.

I never liked the Last Battle Star Galactica series but I did like the first Battle Star Galactica series. Hope you are watching the current Star Trek: Discovery and Star Trek Picard. I like them both. I too tended to prefer the Christopher Reeve Superman (strange coinicidece that George Reeves played Superman on TV decades ago). However, I did like Henry Cavill as Superman as well for some strange reason. I thought Erica Durance was the best looking Lois Lane though the others weren't bad. I have a penchant for brunettes.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by palinka » 2020-11-28 18:15

SorenR wrote:
2020-11-27 19:38
You are free to do whatever you like BUT standards are made to be followed and separate the amateur from the professional...

"This is the way"
Is there such thing as an Amaressional? Promateur? :mrgreen:

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by mattg » 2020-11-28 23:25

jim.bus wrote:
2020-11-27 21:16
See this link.

https://www.hmailserver.com/documentati ... to_install

I believe the information in this hMailServer link is incorrectly stated and should be changed back to what the correct Port Encryption settings are. As you say, for instance, Port 110 is supposed to be unencrypted. But hMailServer Help Documentation indicates it should be Encrypted which is incorrect.
I will think about how to word changes

Personally I believe that port 110 = StartTLS required is appropriate if you have a certificate

I'm going to check on the 'Require SSL/TLS for auth' being the default - I'd expect that should catch many hundreds of people out, which doesn't seem to be the case.
Just 'cause I link to a page and say little else doesn't mean I am not being nice.
https://www.hmailserver.com/documentation

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by jim.bus » 2020-11-29 00:18

mattg wrote:
2020-11-28 23:25
jim.bus wrote:
2020-11-27 21:16
See this link.

https://www.hmailserver.com/documentati ... to_install

I believe the information in this hMailServer link is incorrectly stated and should be changed back to what the correct Port Encryption settings are. As you say, for instance, Port 110 is supposed to be unencrypted. But hMailServer Help Documentation indicates it should be Encrypted which is incorrect.
I will think about how to word changes

Personally I believe that port 110 = StartTLS required is appropriate if you have a certificate

I'm going to check on the 'Require SSL/TLS for auth' being the default - I'd expect that should catch many hundreds of people out, which doesn't seem to be the case.
As I indicated, I personally for my own hMailServer want to require all connections to be Secure no matter which Port is used. So, I set my Port Assignments as such as well since I'm the only Client User of my hMailServer. But I believe the RFCs unless they have changed indicate that Port 25, 110, and 143 are for unsecured unencrypted connections and this is what I mean by the Standards and I believe sorenr was probably referring to the RFCs as well but that is an assumption on my part. I am mostly an Outlook Client user myself and that is where I first learned what the 'Standard' Port encryption usage was. I seem to remember reading that Port 465 was changed some time ago in what it was designated for but for legacy purposes it was still being used for SMTP Encrypted Client connections.

So to be consistent with what is probably specified by the RFCs, I thought the hMailServer Help Documentation should reflect what is currently stated in the RFCs assuming the RFCs are different from what the hMailServer Help Documentation currently states. I believe at least as far as the Documentation and any Default Settings in hMailServer are concerned, hMailServer should be RFC Compliant. Individual installations can customize if it is desired but the RFC Standards should be the Default and what is specified in the Help Documentation are my thoughts. This way when hMailServer is installed by someone there won't be a conflict in the expected way hMailServer behaves in regards to advertised RFC Standards.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by SorenR » 2020-11-29 00:44

mattg wrote:
2020-11-28 23:25
jim.bus wrote:
2020-11-27 21:16
See this link.

https://www.hmailserver.com/documentati ... to_install

I believe the information in this hMailServer link is incorrectly stated and should be changed back to what the correct Port Encryption settings are. As you say, for instance, Port 110 is supposed to be unencrypted. But hMailServer Help Documentation indicates it should be Encrypted which is incorrect.
I will think about how to word changes

Personally I believe that port 110 = StartTLS required is appropriate if you have a certificate

I'm going to check on the 'Require SSL/TLS for auth' being the default - I'd expect that should catch many hundreds of people out, which doesn't seem to be the case.
Well, these are the standards according to IANA ... Yes, there is no "SMTPS".

Optional STARTTLS but NOT a requirement:
- SMTP: Port 25

Optional STARTTLS but NOT a requirement:
- POP3: Port 110
- IMAP: Port 143
- SUBMISSION: Port 587

Required SSL/TLS:
- POP3S: Port 995
- IMAPS: Port 993
- SUBMISSIONS: Port 465

Updated 24. November 2020
https://www.iana.org/assignments/servic ... bers.xhtml
SørenR.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by jim.bus » 2020-11-29 01:25

SorenR wrote:
2020-11-29 00:44
mattg wrote:
2020-11-28 23:25
jim.bus wrote:
2020-11-27 21:16
See this link.

https://www.hmailserver.com/documentati ... to_install

I believe the information in this hMailServer link is incorrectly stated and should be changed back to what the correct Port Encryption settings are. As you say, for instance, Port 110 is supposed to be unencrypted. But hMailServer Help Documentation indicates it should be Encrypted which is incorrect.
I will think about how to word changes

Personally I believe that port 110 = StartTLS required is appropriate if you have a certificate

I'm going to check on the 'Require SSL/TLS for auth' being the default - I'd expect that should catch many hundreds of people out, which doesn't seem to be the case.
Well, these are the standards according to IANA ... Yes, there is no "SMTPS".

Optional STARTTLS but NOT a requirement:
- SMTP: Port 25

Optional STARTTLS but NOT a requirement:
- POP3: Port 110
- IMAP: Port 143
- SUBMISSION: Port 587

Required SSL/TLS:
- POP3S: Port 995
- IMAPS: Port 993
- SUBMISSIONS: Port 465

Updated 24. November 2020
https://www.iana.org/assignments/servic ... bers.xhtml
I indicated it was the RFCs but I wasn't sure where I had seen it. IANA therefore is probably the 'authoritative source' then. I notice though the IANA standard was updated 4 days ago so now we know the current 'Standard'. Therefore, I would say the hMailServer Help Documentation and/or Defaults should be consistent with the IANA Standard.

But interesting is that Outlook 365 still allows Port 465 to use StartTLS but then Outlook 365 might not be updated quite yet or maybe not for a long time. There are other discrepancies in Outlook 365 perhaps as well.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by SorenR » 2020-11-29 02:19

jim.bus wrote:
2020-11-29 01:25
But interesting is that Outlook 365 still allows Port 465 to use StartTLS but then Outlook 365 might not be updated quite yet or maybe not for a long time. There are other discrepancies in Outlook 365 perhaps as well.
Port 465 is fine with STARTTLS or SSL as long as it is either. It cannot be unencryptet.
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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by palinka » 2020-11-29 21:40

SorenR wrote:
2020-11-29 02:19
jim.bus wrote:
2020-11-29 01:25
But interesting is that Outlook 365 still allows Port 465 to use StartTLS but then Outlook 365 might not be updated quite yet or maybe not for a long time. There are other discrepancies in Outlook 365 perhaps as well.
Port 465 is fine with STARTTLS or SSL as long as it is either. It cannot be unencryptet.
Some clients won't do startTLS on 465.

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Re: MS Outlook Professional Plus 2019, POP3 Fail

Post by SorenR » 2020-11-29 22:00

palinka wrote:
2020-11-29 21:40
SorenR wrote:
2020-11-29 02:19
jim.bus wrote:
2020-11-29 01:25
But interesting is that Outlook 365 still allows Port 465 to use StartTLS but then Outlook 365 might not be updated quite yet or maybe not for a long time. There are other discrepancies in Outlook 365 perhaps as well.
Port 465 is fine with STARTTLS or SSL as long as it is either. It cannot be unencryptet.
Some clients won't do startTLS on 465.
As we say @home; No arms, No cookies.
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Algorithm (noun.)
Word used by programmers when they do not want to explain what they did.

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