Ok, here goes. 
tls-debug 1
2022-02-21 10:34:11 dirmngr[17092] listening on socket ‘C:\Users\Kim\AppData\Local\gnupg\S.dirmngr’
2022-02-21 10:34:12 dirmngr[17092] permanently loaded certificates: 180
2022-02-21 10:34:12 dirmngr[17092] runtime cached certificates: 0
2022-02-21 10:34:12 dirmngr[17092] trusted certificates: 180 (180,0,0,0)
2022-02-21 10:34:12 dirmngr[17092] handler for fd 712 started
2022-02-21 10:34:12 dirmngr[17092] resolve_dns_addr for ‘keyserver.ubuntu.com’: ‘162.213.33.9’
2022-02-21 10:34:12 dirmngr[17092] resolve_dns_addr for ‘keyserver.ubuntu.com’: ‘162.213.33.8’
2022-02-21 10:34:12 dirmngr[17092] detected interfaces: IPv4
2022-02-21 10:34:12 dirmngr[17092] DBG: ntbtls(1): server_hello, chosen version: [3:3]
2022-02-21 10:34:12 dirmngr[17092] DBG: ntbtls(1): server_hello, chosen ciphersuite: 49199 (TLS-ECDHE-RSA-WITH-AES-128-GCM-SHA256)
2022-02-21 10:34:12 dirmngr[17092] ntbtls: peer certificate: chain length=3
2022-02-21 10:34:12 dirmngr[17092] DBG: ntbtls(1): comparing hostname ‘hockeypuck.ubuntu.com’ to ‘keyserver.ubuntu.com’
2022-02-21 10:34:12 dirmngr[17092] DBG: ntbtls(1): comparing hostname ‘keyserver.ubuntu.com’ to ‘keyserver.ubuntu.com’
2022-02-21 10:34:12 dirmngr[17092] certificate already cached
2022-02-21 10:34:12 dirmngr[17092] certificate cached
2022-02-21 10:34:12 dirmngr[17092] Note: non-critical certificate policy not allowed
2022-02-21 10:34:12 dirmngr[17092] certificate is good
2022-02-21 10:34:12 dirmngr[17092] certificate has expired
2022-02-21 10:34:12 dirmngr[17092] (expired at 2021-09-29 19:21:40)
2022-02-21 10:34:12 dirmngr[17092] Note: non-critical certificate policy not allowed
2022-02-21 10:34:12 dirmngr[17092] certificate is good
2022-02-21 10:34:12 dirmngr[17092] certificate has expired
2022-02-21 10:34:12 dirmngr[17092] (expired at 2021-09-30 14:01:15)
2022-02-21 10:34:12 dirmngr[17092] root certificate is good and trusted
2022-02-21 10:34:12 dirmngr[17092] target certificate is NOT valid
2022-02-21 10:34:12 dirmngr[17092] DBG: ntbtls(1): error from the verify callback returned: Certificate expired
2022-02-21 10:34:12 dirmngr[17092] TLS handshake failed: Certificate expired
2022-02-21 10:34:12 dirmngr[17092] error connecting to ‘https://162.213.33.8:443’: Certificate expired
2022-02-21 10:34:12 dirmngr[17092] command ‘KS_SEARCH’ failed: Certificate expired
2022-02-21 10:34:12 dirmngr[17092] handler for fd 712 terminated
tls-debug 2
2022-02-21 10:35:46 dirmngr[22880] listening on socket ‘C:\Users\Kim\AppData\Local\gnupg\S.dirmngr’
2022-02-21 10:35:46 dirmngr[22880] permanently loaded certificates: 180
2022-02-21 10:35:46 dirmngr[22880] runtime cached certificates: 0
2022-02-21 10:35:46 dirmngr[22880] trusted certificates: 180 (180,0,0,0)
2022-02-21 10:35:46 dirmngr[22880] handler for fd 708 started
2022-02-21 10:35:46 dirmngr[22880] resolve_dns_addr for ‘keyserver.ubuntu.com’: ‘162.213.33.9’
2022-02-21 10:35:46 dirmngr[22880] resolve_dns_addr for ‘keyserver.ubuntu.com’: ‘162.213.33.8’
2022-02-21 10:35:46 dirmngr[22880] detected interfaces: IPv4
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): handshake
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): client state: 0 (hello_request)
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): client state: 1 (client_hello)
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): write client_hello
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): client state: 2 (server_hello)
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): read server_hello
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(1): server_hello, chosen version: [3:3]
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(1): server_hello, chosen ciphersuite: 49199 (TLS-ECDHE-RSA-WITH-AES-128-GCM-SHA256)
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): server_hello, total extension length: 21
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): found renegotiation extension
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): unknown extension found: 0 (ignoring)
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): found supported_point_formats extension
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): found session_ticket extension
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): client state: 3 (server_certificate)
2022-02-21 10:35:46 dirmngr[22880] ntbtls: peer certificate: chain length=3
2022-02-21 10:35:46 dirmngr[22880]ntbtls: serial: 04cc227c37c5112c6c1b538b751a18451bf6
2022-02-21 10:35:46 dirmngr[22880] ntbtls: issuer: CN=R3,O=Let’s Encrypt,C=US
2022-02-21 10:35:46 dirmngr[22880] ntbtls: subject: CN=hockeypuck.ubuntu.com
2022-02-21 10:35:46 dirmngr[22880] ntbtls: aka: (8:dns-name21:hockeypuck.ubuntu.com)
2022-02-21 10:35:46 dirmngr[22880] ntbtls: aka: (8:dns-name20:keyserver.ubuntu.com)
2022-02-21 10:35:46 dirmngr[22880] ntbtls: notBefore: 2021-12-25 03:20:36
2022-02-21 10:35:46 dirmngr[22880] ntbtls: notAfter: 2022-03-25 03:20:35
2022-02-21 10:35:46 dirmngr[22880] ntbtls: hashAlgo: 1.2.840.113549.1.1.11
2022-02-21 10:35:46 dirmngr[22880]ntbtls: serial: 00912b084acf0c18a753f6d62e25a75f5a
2022-02-21 10:35:46 dirmngr[22880] ntbtls: issuer: CN=ISRG Root X1,O=Internet Security Research Group,C=US
2022-02-21 10:35:46 dirmngr[22880] ntbtls: subject: CN=R3,O=Let’s Encrypt,C=US
2022-02-21 10:35:46 dirmngr[22880] ntbtls: notBefore: 2020-09-04 00:00:00
2022-02-21 10:35:46 dirmngr[22880] ntbtls: notAfter: 2025-09-15 16:00:00
2022-02-21 10:35:46 dirmngr[22880] ntbtls: hashAlgo: 1.2.840.113549.1.1.11
2022-02-21 10:35:46 dirmngr[22880]ntbtls: serial: 4001772137d4e942b8ee76aa3c640ab7
2022-02-21 10:35:46 dirmngr[22880] ntbtls: issuer: CN=DST Root CA X3,O=Digital Signature Trust Co.
2022-02-21 10:35:46 dirmngr[22880] ntbtls: subject: CN=ISRG Root X1,O=Internet Security Research Group,C=US
2022-02-21 10:35:46 dirmngr[22880] ntbtls: notBefore: 2021-01-20 19:14:03
2022-02-21 10:35:46 dirmngr[22880] ntbtls: notAfter: 2024-09-30 18:14:03
2022-02-21 10:35:46 dirmngr[22880] ntbtls: hashAlgo: 1.2.840.113549.1.1.11
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(1): comparing hostname ‘hockeypuck.ubuntu.com’ to ‘keyserver.ubuntu.com’
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(1): comparing hostname ‘keyserver.ubuntu.com’ to ‘keyserver.ubuntu.com’
2022-02-21 10:35:46 dirmngr[22880] certificate already cached
2022-02-21 10:35:46 dirmngr[22880] certificate cached
2022-02-21 10:35:46 dirmngr[22880] Note: non-critical certificate policy not allowed
2022-02-21 10:35:46 dirmngr[22880] certificate is good
2022-02-21 10:35:46 dirmngr[22880] certificate has expired
2022-02-21 10:35:46 dirmngr[22880] (expired at 2021-09-29 19:21:40)
2022-02-21 10:35:46 dirmngr[22880] Note: non-critical certificate policy not allowed
2022-02-21 10:35:46 dirmngr[22880] certificate is good
2022-02-21 10:35:46 dirmngr[22880] certificate has expired
2022-02-21 10:35:46 dirmngr[22880] (expired at 2021-09-30 14:01:15)
2022-02-21 10:35:46 dirmngr[22880] root certificate is good and trusted
2022-02-21 10:35:46 dirmngr[22880] target certificate is NOT valid
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(1): error from the verify callback returned: Certificate expired
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): handshake ready
2022-02-21 10:35:46 dirmngr[22880] TLS handshake failed: Certificate expired
2022-02-21 10:35:46 dirmngr[22880] error connecting to ‘https://162.213.33.8:443’: Certificate expired
2022-02-21 10:35:46 dirmngr[22880] DBG: ntbtls(2): release
2022-02-21 10:35:46 dirmngr[22880] command ‘KS_SEARCH’ failed: Certificate expired
2022-02-21 10:35:46 dirmngr[22880] handler for fd 708 terminated
tls-debug 3
2022-02-21 10:40:31 dirmngr[2592] listening on socket ‘C:\Users\Kim\AppData\Local\gnupg\S.dirmngr’
2022-02-21 10:40:31 dirmngr[2592] permanently loaded certificates: 180
2022-02-21 10:40:31 dirmngr[2592] runtime cached certificates: 0
2022-02-21 10:40:31 dirmngr[2592] trusted certificates: 180 (180,0,0,0)
2022-02-21 10:40:31 dirmngr[2592] handler for fd 720 started
2022-02-21 10:40:31 dirmngr[2592] resolve_dns_addr for ‘keyserver.ubuntu.com’: ‘162.213.33.9’
2022-02-21 10:40:31 dirmngr[2592] resolve_dns_addr for ‘keyserver.ubuntu.com’: ‘162.213.33.8’
2022-02-21 10:40:31 dirmngr[2592] detected interfaces: IPv4
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): handshake
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): client state: 0 (hello_request)
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): flush output
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): client state: 1 (client_hello)
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): flush output
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): write client_hello
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, max version: [3:3]
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, current time: 1645436431
2022-02-21 10:40:31 dirmngr[2592] DBG: client_hello, random bytes: 62135e0f392dc4c64d93cd9d246245268727da03abf349002ac3e54038f381a1
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, session id len.: 0
2022-02-21 10:40:31 dirmngr[2592] DBG: client_hello, session id:
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, got 78 ciphersuites
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, compress len.: 2
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, compress alg.: 1 0
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, adding server name extension: ‘keyserver.ubuntu.com’
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, adding signature_algorithms extension
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client hello, adding supported_elliptic_curves extension
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client hello, adding supported_point_formats extension
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, adding session ticket extension
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): client_hello, total extension length: 83
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): write record
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): output record: msgtype = 22, version = [3:3], msglen = 285
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): flush output
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): message length: 290, out_left: 290
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): es_write returned: success
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): client state: 2 (server_hello)
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): flush output
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): read server_hello
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): read record
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): fetch input
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): in_left: 0, nb_want: 5
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): es_read returned: success
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): input record: msgtype = 22, version = [3:3], msglen = 65
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): fetch input
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): in_left: 5, nb_want: 70
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): es_read returned: success
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): handshake message: msglen = 65, type = 2, hslen = 65
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(1): server_hello, chosen version: [3:3]
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): server_hello, current time: 2411400778
2022-02-21 10:40:31 dirmngr[2592] DBG: server_hello, random bytes: 8fbb0e4a0803168a8830148b455259b7d8239aa390d8cf50444f574e47524401
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): server_hello, session id len.: 0
2022-02-21 10:40:31 dirmngr[2592] DBG: server_hello, session id:
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): no session has been resumed
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(1): server_hello, chosen ciphersuite: 49199 (TLS-ECDHE-RSA-WITH-AES-128-GCM-SHA256)
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): server_hello, compress alg.: 0
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): server_hello, total extension length: 21
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): found renegotiation extension
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): unknown extension found: 0 (ignoring)
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): found supported_point_formats extension
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): found session_ticket extension
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): client state: 3 (server_certificate)
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): flush output
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): read certificate
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): read record
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): fetch input
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): in_left: 0, nb_want: 5
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): es_read returned: success
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): input record: msgtype = 22, version = [3:3], msglen = 4056
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): fetch input
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): in_left: 5, nb_want: 4061
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): es_read returned: success
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(3): handshake message: msglen = 4056, type = 11, hslen = 4056
2022-02-21 10:40:31 dirmngr[2592] ntbtls: peer certificate: chain length=3
2022-02-21 10:40:31 dirmngr[2592]ntbtls: serial: 04cc227c37c5112c6c1b538b751a18451bf6
2022-02-21 10:40:31 dirmngr[2592] ntbtls: issuer: CN=R3,O=Let’s Encrypt,C=US
2022-02-21 10:40:31 dirmngr[2592] ntbtls: subject: CN=hockeypuck.ubuntu.com
2022-02-21 10:40:31 dirmngr[2592] ntbtls: aka: (8:dns-name21:hockeypuck.ubuntu.com)
2022-02-21 10:40:31 dirmngr[2592] ntbtls: aka: (8:dns-name20:keyserver.ubuntu.com)
2022-02-21 10:40:31 dirmngr[2592] ntbtls: notBefore: 2021-12-25 03:20:36
2022-02-21 10:40:31 dirmngr[2592] ntbtls: notAfter: 2022-03-25 03:20:35
2022-02-21 10:40:31 dirmngr[2592] ntbtls: hashAlgo: 1.2.840.113549.1.1.11
2022-02-21 10:40:31 dirmngr[2592]ntbtls: serial: 00912b084acf0c18a753f6d62e25a75f5a
2022-02-21 10:40:31 dirmngr[2592] ntbtls: issuer: CN=ISRG Root X1,O=Internet Security Research Group,C=US
2022-02-21 10:40:31 dirmngr[2592] ntbtls: subject: CN=R3,O=Let’s Encrypt,C=US
2022-02-21 10:40:31 dirmngr[2592] ntbtls: notBefore: 2020-09-04 00:00:00
2022-02-21 10:40:31 dirmngr[2592] ntbtls: notAfter: 2025-09-15 16:00:00
2022-02-21 10:40:31 dirmngr[2592] ntbtls: hashAlgo: 1.2.840.113549.1.1.11
2022-02-21 10:40:31 dirmngr[2592]ntbtls: serial: 4001772137d4e942b8ee76aa3c640ab7
2022-02-21 10:40:31 dirmngr[2592] ntbtls: issuer: CN=DST Root CA X3,O=Digital Signature Trust Co.
2022-02-21 10:40:31 dirmngr[2592] ntbtls: subject: CN=ISRG Root X1,O=Internet Security Research Group,C=US
2022-02-21 10:40:31 dirmngr[2592] ntbtls: notBefore: 2021-01-20 19:14:03
2022-02-21 10:40:31 dirmngr[2592] ntbtls: notAfter: 2024-09-30 18:14:03
2022-02-21 10:40:31 dirmngr[2592] ntbtls: hashAlgo: 1.2.840.113549.1.1.11
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(1): comparing hostname ‘hockeypuck.ubuntu.com’ to ‘keyserver.ubuntu.com’
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(1): comparing hostname ‘keyserver.ubuntu.com’ to ‘keyserver.ubuntu.com’
2022-02-21 10:40:31 dirmngr[2592] certificate already cached
2022-02-21 10:40:31 dirmngr[2592] certificate cached
2022-02-21 10:40:31 dirmngr[2592] Note: non-critical certificate policy not allowed
2022-02-21 10:40:31 dirmngr[2592] certificate is good
2022-02-21 10:40:31 dirmngr[2592] certificate has expired
2022-02-21 10:40:31 dirmngr[2592] (expired at 2021-09-29 19:21:40)
2022-02-21 10:40:31 dirmngr[2592] Note: non-critical certificate policy not allowed
2022-02-21 10:40:31 dirmngr[2592] certificate is good
2022-02-21 10:40:31 dirmngr[2592] certificate has expired
2022-02-21 10:40:31 dirmngr[2592] (expired at 2021-09-30 14:01:15)
2022-02-21 10:40:31 dirmngr[2592] root certificate is good and trusted
2022-02-21 10:40:31 dirmngr[2592] target certificate is NOT valid
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(1): error from the verify callback returned: Certificate expired
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): handshake ready
2022-02-21 10:40:31 dirmngr[2592] TLS handshake failed: Certificate expired
2022-02-21 10:40:31 dirmngr[2592] error connecting to ‘https://162.213.33.8:443’: Certificate expired
2022-02-21 10:40:31 dirmngr[2592] DBG: ntbtls(2): release
2022-02-21 10:40:31 dirmngr[2592] command ‘KS_SEARCH’ failed: Certificate expired
2022-02-21 10:40:31 dirmngr[2592] handler for fd 720 terminated
tls-debug 4 - eh, that’s so long it deserves its own post.