Thanks to all who responded for your feedback.

Unfortunately, the firewall blocking outbound traffic isn't something I can do 
anything about. Servers in our "web zone" must have specific rules allowing 
outbound access. That's fine for Red Hat or Ubuntu repositories but this is the 
first machine where we are trying to install using pip, so getting the right 
rule in place took some experimentation and adjustment.

I did eventually get the install to work with the firewall opened for me and 
with a --proxy option added to the command (although I'm not 100% sure --proxy 
was needed). 

The other thing I had to do that was different to the instructions was to use 
pip to install setuptools. I got to a point where I had an error message that 
said "ERROR: Could not find a version that satisfies the requirement 
setuptools>=40.8.0" but when I ran "apt install python3-setuptools" it reported 
that it was "already the newest version (68.1.2-2ubuntu1.2)". However, running 
pip install setuptools (on a whim) installed version 80.9.0. After that "pip 
install mailman" worked. Perhaps I should have known this. I feel that making 
sure setuptools is properly installed might be something to add to the 
installation instructions.

The next step in the instructions has me create /etc/mailman3/mailman.cfg. The 
first thing in that file is shown as:

[paths.here]
var_dir: /opt/mailman/mm/var

Looking in /opt/mailman, there is no mm directory. Should that have been 
created, or is that something I need to create myself?

-- 
Henry Hartley
Westat
RB 2151

-----Original Message-----
From: Gerald Vogt <v...@spamcop.net> 
Sent: Tuesday, June 3, 2025 12:29
To: mailman-users@mailman3.org
Subject: [MM3-users] Re: Trouble Installing Mailman3

CAUTION: External Email *


On 03.06.25 17:22, Henry Hartley via Mailman-users wrote:
> I'm having problems installing mailman3 following the instructions on 
> https://secure-web.cisco.com/1lGZ6VhIpDXnBDYduOpQfdrz5vzmVmUu1Ox4qpxrEdA3f2KDMfSAg-Y0dIstuex-9FpNTp4I-1u9_EPifC-KC3henFw5joPUkxkGPwo-q6Nq3HjaOJk-_RaH0MxxZW4dMtrBe-R3scY2sQvyYQsIRPMmmlqyT2bhhwoO5FkJEIA0g5XOZkpc8hQpNtYEyk9dDawfMAls9Fj-UVCiXTXbwMw_NbWQwc3n-sDc-BrUEbmqPu_6yXsaHb8i8G23M-T8-/https%3A%2F%2Fdocs.mailman3.org%2Fen%2Flatest%2Finstall%2Fvirtualenv.html
>  Everything goes well until I get to the Installing Mailman 
> Core<https://secure-web.cisco.com/1XnIv9oM-wXrdCe9VFieDJykhtB-NNf5h-UB4ysN7pvWtAsS6fCdxn5vghY2GKjLzSHxQvrkI0p1yYPcE3C4GDaO1wujxMvmz0W_f-WFxuilDLY5HZHarcxHWSu3Ow6tuzURhd4OQlShOlKBFcmEyuL5QD-9C-ZBUDVnqOcJUalzAqUgqF4rmQuRiIdVVOVZ48Dnbbqyh2zFpADQ2dZblEpwGW0LyIIvtm9McnuL316qPT7eXCt6-NqJ_Qivxr0M7/https%3A%2F%2Fdocs.mailman3.org%2Fen%2Flatest%2Finstall%2Fvirtualenv.html%23installing-mailman-core>
>  step, which has me do the following in my venv environment:
>
> (venv)$ pip install wheel mailman psycopg2-binary
>
> Ubuntu 24.04.02 LTS
> Python 3.12.3
> pip version 24.0
>
> First, I was getting problems because my company firewall was blocking 
> outbound traffic. I got that taken care of. Next, I was seeing certificate 
> errors, saying there was a self-signed certificate:
>
> WARNING: Retrying (Retry(total=0, connect=None, read=None, 
> redirect=None, status=None)) after connection broken by 
> 'SSLError(SSLCertVerificationError(1, '[SSL: 
> CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed 
> certificate in certificate chain (_ssl.c:1000)'))': /simple/wheel/ 
> Could not fetch URL 
> https://secure-web.cisco.com/149I_kjrnLhuIpr1APuB8udvv8jCJuk0lqcI_esQ-
> dqwmKVpgaw1Y6LT5_dF8kBkxoIp3E5cH7c8E3NU5TFqaenv2yCcBV0jBYVDBuHgpqP9oRU
> OfJ6XZruLMDf2pqH2ydyrnAxjJ_ZTs59eeLe69Iy0jFuoA5d_XpSiBVdVvGKbBN13EkyH2
> HNcgmruVikAcwrT6sN52QPqQIesisnHaK6MvxqVRbMuHjoY3vpvMzLsJaSrN6_XOSx3oGf
> DZgAOV/https%3A%2F%2Fpypi.org%2Fsimple%2Fwheel%2F%3A There was a 
> problem confirming the ssl certificate: 
> HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded 
> with url: /simple/wheel/ (Caused by 
> SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] 
> certificate verify failed: self-signed certificate in certificate 
> chain (_ssl.c:1000)'))) - skipping

There is no self-signed certificate in the chain, when I check it. I guess, 
there is a proxy somewhere which has a different certificate.

Run

$ openssl s_client -connect pypi.org:443 -showcerts

to check what certificate is presented. It should be something like:

Connecting to 2a04:4e42::223
CONNECTED(00000003)
depth=2 OU=GlobalSign Root CA - R3, O=GlobalSign, CN=GlobalSign verify return:1
depth=1 C=BE, O=GlobalSign nv-sa, CN=GlobalSign Atlas R3 DV TLS CA 2025 Q1 
verify return:1
depth=0 CN=pypi.org
verify return:1
---
Certificate chain
  0 s:CN=pypi.org
    i:C=BE, O=GlobalSign nv-sa, CN=GlobalSign Atlas R3 DV TLS CA 2025 Q1
    a:PKEY: rsaEncryption, 2048 (bit); sigalg: RSA-SHA256
    v:NotBefore: Feb 24 04:28:22 2025 GMT; NotAfter: Mar 28 04:28:21
2026 GMT
...
  1 s:C=BE, O=GlobalSign nv-sa, CN=GlobalSign Atlas R3 DV TLS CA 2025 Q1
    i:OU=GlobalSign Root CA - R3, O=GlobalSign, CN=GlobalSign
    a:PKEY: rsaEncryption, 2048 (bit); sigalg: RSA-SHA256
    v:NotBefore: Oct 16 03:08:04 2024 GMT; NotAfter: Oct 16 00:00:00
2026 GMT
...
Server certificate
subject=CN=pypi.org
issuer=C=BE, O=GlobalSign nv-sa, CN=GlobalSign Atlas R3 DV TLS CA 2025 Q1 ...

> When I added --trusted-host pypi.org that error went away but I'm still 
> unable to install anything:

Never ever do that. Find out what is happening. Either something bad is 
interfering with your network traffic. Or there is a proxy and the chain is 
different. In the latter case, you will see lots of issue until you have 
configured your system correctly for the proxy in place...

But never ever simply turn off security and try to install something through 
broken security. It defies the whole purpose of security and certificates if 
you simply turn it off or try to ignore it.

-Gerald
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