There is still something wrong here. The site in question has fixed the issue in response to my query, and SSL Labs now gives it an A grade:
https://www.ssllabs.com/ssltest/analyze.html?d=www.toodledo.com According to SSL Labs, it supports these two ciphers for TLS 1.2: TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 (0xc030) TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (0xc02f) According to openssl ciphers -s -V, both of these are supported by openssl: $ openssl ciphers -s -V | egrep '0xC0,0x(30|2F)' 0xC0,0x30 - ECDHE-RSA-AES256-GCM-SHA384 TLSv1.2 Kx=ECDH Au=RSA Enc=AESGCM(256) Mac=AEAD 0xC0,0x2F - ECDHE-RSA-AES128-GCM-SHA256 TLSv1.2 Kx=ECDH Au=RSA Enc=AESGCM(128) Mac=AEAD And yet I'm still unable to connect to this server through openssl unless I downgrade the security level to 1. You mentioned there being an SHA1 certificate in the chain, but I don't see one. The certs all seem to be SHA256. I cannot find any evidence that security level 2 blocks the use of certificates with lifetimes of more than a year. Is that an undocumented "feature" of security level 2? -- You received this bug notification because you are a member of Ubuntu Touch seeded packages, which is subscribed to openssl in Ubuntu. https://bugs.launchpad.net/bugs/1864689 Title: openssl in 20.04 can't connect to site that was fine in 19.10 and is fine in Chrome and Firefox Status in openssl package in Ubuntu: New Bug description: openssl in Ubuntu 20.04 (focal) refuses to connect to a web site that openssl in Ubuntu 19.10 (eoan), Chrome, and Firefox are all happy to connect to. Reproduce with: `curl -v https://www.toodledo.com/' or: `openssl s_client -connect www.toodledo.com:443` or: `python3 -c 'import requests; requests.get("https://www.toodledo.com/")'` or: `wget https://www.toodledo.com/` These worked in Ubuntu 19.10 and don't work in 20.04. I've tried all sorts of things to debug this further and I've just run into walls. I hope someone who understands more about this stuff will be able to figure it out. ProblemType: Bug DistroRelease: Ubuntu 20.04 Package: openssl 1.1.1d-2ubuntu3 ProcVersionSignature: Ubuntu 5.4.0-14.17-generic 5.4.18 Uname: Linux 5.4.0-14-generic x86_64 ApportVersion: 2.20.11-0ubuntu18 Architecture: amd64 CurrentDesktop: ubuntu:GNOME Date: Tue Feb 25 13:01:22 2020 InstallationDate: Installed on 2019-08-16 (192 days ago) InstallationMedia: Ubuntu 19.04 "Disco Dingo" - Release amd64 (20190416) SourcePackage: openssl UpgradeStatus: Upgraded to focal on 2020-01-31 (25 days ago) To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssl/+bug/1864689/+subscriptions -- Mailing list: https://launchpad.net/~touch-packages Post to : touch-packages@lists.launchpad.net Unsubscribe : https://launchpad.net/~touch-packages More help : https://help.launchpad.net/ListHelp