Something does not add up here.

High Sierra is older than Mojave, right? I can fetch sources of nsd on High 
Sierra without any problems:

$ sudo port -d fetch nsd    
DEBUG: Copying /Users/pike/Library/Preferences/com.apple.dt.Xcode.plist to 
/opt/local/var/macports/home/Library/Preferences
DEBUG: Changing to port directory: 
/opt/local/var/macports/sources/rsync.macports.org/macports/release/tarballs/ports/net/nsd
DEBUG: OS darwin/17.7.0 (macOS 10.13.6) arch i386
DEBUG: adding the default universal variant
DEBUG: Reading variant descriptions from 
/opt/local/var/macports/sources/rsync.macports.org/macports/release/tarballs/ports/_resources/port1.0/variant_descriptions.conf
DEBUG: Running callback portconfigure::add_automatic_compiler_dependencies
DEBUG: Finished running callback 
portconfigure::add_automatic_compiler_dependencies
DEBUG: Running callback portbuild::add_automatic_buildsystem_dependencies
DEBUG: Finished running callback 
portbuild::add_automatic_buildsystem_dependencies
DEBUG: Running callback portstartupitem::add_notes
DEBUG: Finished running callback portstartupitem::add_notes
DEBUG: Attempting ln -sf 
/opt/local/var/macports/build/_opt_local_var_macports_sources_rsync.macports.org_macports_release_tarballs_ports_net_nsd/nsd/work
 
/opt/local/var/macports/sources/rsync.macports.org/macports/release/tarballs/ports/net/nsd/work
DEBUG: dropping privileges: euid changed to 504, egid changed to 20.
DEBUG: Starting logging for nsd @4.2.1_2
DEBUG: macOS 10.13.6 (darwin/17.7.0) arch i386
DEBUG: MacPorts 2.7.1
DEBUG: Xcode 9.4.1
DEBUG: SDK 10.13
DEBUG: MACOSX_DEPLOYMENT_TARGET: 10.13
DEBUG: Executing org.macports.main (nsd)
DEBUG: dropping privileges: euid changed to 504, egid changed to 20.
DEBUG: fetch phase started at Sat Nov  6 19:00:42 PDT 2021
--->  Fetching distfiles for nsd
DEBUG: elevating privileges for fetch: euid changed to 0, egid changed to 0.
DEBUG: dropping privileges: euid changed to 504, egid changed to 20.
DEBUG: Executing org.macports.fetch (nsd)
--->  nsd-4.2.1.tar.gz does not exist in /opt/local/var/macports/distfiles/nsd
--->  Attempting to fetch nsd-4.2.1.tar.gz from 
http://distfiles.macports.org/nsd
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100 1118k  100 1118k    0     0  3557k      0 --:--:-- --:--:-- --:--:-- 3563k
$ ls -l /opt/local/var/macports/distfiles/nsd
total 2240
-rw-r--r--  1 macports  wheel  1145713 Nov  6 19:00 nsd-4.2.1.tar.gz

I have MacPorts installed from a package, I did not build it, so it is pretty 
much standard. Neither I did anything to the system certificate chain.

> On Nov 6, 2021, at 5:43 AM, Ryan Schmidt <ryandes...@macports.org> wrote:
> 
> 
> 
> On Nov 6, 2021, at 05:39, Gerben Wierda wrote:
> 
>> I was looking at updating nsd (for which I am maintaining and it is high 
>> time)
>> 
>> But fetching failed on macOS Mojave (where I have my MacPorts setup).
>> 
>> :debug:fetch Executing org.macports.fetch (nsd)
>> :info:fetch --->  nsd-4.3.8.tar.gz does not exist in 
>> /opt/local/var/macports/distfiles/nsd
>> :notice:fetch --->  Attempting to fetch nsd-4.3.8.tar.gz from 
>> https://www.nlnetlabs.nl/downloads/nsd/
>> :debug:fetch Fetching distfile failed: SSL certificate problem: certificate 
>> has expired
>> 
>> Now, my main MacPorts dev/use machine is macOS Mojave so I suspect that is 
>> the Mojave-doesn’t-get-root-cert-updates problem. So, I tried to do a port 
>> fetch on Catalina, and there it works and the distribution is downloaded.
>> 
>> It is strange, though, because Safari on both Catalina (other machine) and 
>> Mojave say the cert is fine. Still, it is most likely that this is a problem 
>> that comes from still using Mojave.
>> 
>> Updating that machine will not happen until late December, so if I am to 
>> maintain anything MacPorts, I need a fix to get this working again.
>> 
>> I have tried using curl on the Mojave machine, and that one works.
>> 
>> So, Safari works, curl works, but port does not work.
>> 
>> I tried copying /etc/ssl/cert.pem over to the Mojave machine, but that 
>> doesn’t work either.
> 
> This is the "Let's Encrypt's old root certificate expired" problem described 
> here:
> 
> https://trac.macports.org/wiki/ProblemHotlist#letsencrypt
> 
> When you said "curl works but port does not work" that's not quite right. 
> /opt/local/bin/curl and /opt/local/lib/libcurl.dylib work. /usr/bin/curl and 
> /usr/lib/libcurl.dylib (the latter of which MacPorts uses by default) do not 
> work for Let's Encrypt-protected sites anymore.
> 
> I, on High Sierra, have the same issue, and I have no solution for you. This 
> issue affects High Sierra and Mojave. I recommend upgrading to Catalina or 
> later; I plan to eventually.
> 
> Well, you could rebuild MacPorts from source, instructing it to use a newer 
> copy of libcurl with a newer copy of openssl or libressl that has a newer 
> certificate bundle. For example, install a bootstrap copy of MacPorts in a 
> separate prefix, install curl in that prefix, then rebuild your primary 
> MacPorts from source, telling it to use the libcurl in the separate prefix. 
> Any future upgrades to MacPorts base probably also have to be done from 
> source; using "sudo port selfupdate" will not preserve your configure 
> arguments and you'll be back to using the System's broken libcurl again.

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