Reproduced the bug with:

# dpkg-query -W libssl1.0.0 openssl
libssl1.0.0:amd64       1.0.2g-1ubuntu4.19
openssl 1.0.2g-1ubuntu4.19

# openssl s_client -connect expired-root-ca-test.germancoding.com:443 
-servername expired-root-ca-test.germancoding.com -verify 1 -verifyCAfile ca.pem
verify depth is 1
CONNECTED(00000003)
depth=3 C = US, O = (STAGING) Internet Security Research Group, CN = (STAGING) 
Doctored Durian Root CA X3
verify error:num=10:certificate has expired
notAfter=Jan 30 14:01:15 2021 GMT
140540576667288:error:14090086:SSL 
routines:ssl3_get_server_certificate:certificate verify failed:s3_clnt.c:1264:

# upgrading

# dpkg-query -W libssl1.0.0 openssl
libssl1.0.0:amd64       1.0.2g-1ubuntu4.20
openssl 1.0.2g-1ubuntu4.20

# # openssl s_client -connect expired-root-ca-test.germancoding.com:443 
-servername expired-root-ca-test.germancoding.com -verify 1 -verifyCAfile ca.pem
verify depth is 1
CONNECTED(00000003)
depth=2 C = US, O = (STAGING) Internet Security Research Group, CN = (STAGING) 
Pretend Pear X1
verify return:1
depth=1 C = US, O = (STAGING) Let's Encrypt, CN = (STAGING) Artificial Apricot 
R3
verify return:1
depth=0 CN = expired-root-ca-test.germancoding.com
verify return:1
---
Certificate chain
 0 s:/CN=expired-root-ca-test.germancoding.com
   i:/C=US/O=(STAGING) Let's Encrypt/CN=(STAGING) Artificial Apricot R3
 1 s:/C=US/O=(STAGING) Let's Encrypt/CN=(STAGING) Artificial Apricot R3
   i:/C=US/O=(STAGING) Internet Security Research Group/CN=(STAGING) Pretend 
Pear X1
 2 s:/C=US/O=(STAGING) Internet Security Research Group/CN=(STAGING) Pretend 
Pear X1
   i:/C=US/O=(STAGING) Internet Security Research Group/CN=(STAGING) Doctored 
Durian Root CA X3
---
Server certificate
-----BEGIN CERTIFICATE-----
MIIGgTCCBWmgAwIBAgITAPqeXD5BcpT3tXI8aoDSYano7DANBgkqhkiG9w0BAQsF

....

connection is successful.

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https://bugs.launchpad.net/bugs/1928989

Title:
  expiring trust anchor compatibility issue

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