Focal verification a) Secure channel test Reproducing the bug: ubuntu@f-smb-ad:~$ apt-cache policy samba samba: Installed: 2:4.15.13+dfsg-0ubuntu0.20.04.3 Candidate: 2:4.15.13+dfsg-0ubuntu0.20.04.3 Version table: *** 2:4.15.13+dfsg-0ubuntu0.20.04.3 500 500 http://br.archive.ubuntu.com/ubuntu focal-updates/main amd64 Packages 500 http://br.archive.ubuntu.com/ubuntu focal-security/main amd64 Packages 100 /var/lib/dpkg/status Secure channel fails like this: PS C:\Users\focal.SAMBA.002> Test-ComputerSecureChannel -Verbose VERBOSE: Performing the operation "Test-ComputerSecureChannel" on target "DESKTOP-FN048B9". False VERBOSE: The secure channel between the local computer and the domain samba.example is broken. I then apply the samba update to the AD machine, from proposed: ubuntu@f-smb-ad:~$ apt-cache policy samba samba: Installed: 2:4.15.13+dfsg-0ubuntu0.20.04.4 Candidate: 2:4.15.13+dfsg-0ubuntu0.20.04.4 Version table: *** 2:4.15.13+dfsg-0ubuntu0.20.04.4 500 500 http://archive.ubuntu.com/ubuntu focal-proposed/main amd64 Packages 100 /var/lib/dpkg/status 2:4.15.13+dfsg-0ubuntu0.20.04.3 500 500 http://archive.ubuntu.com/ubuntu focal-updates/main amd64 Packages 500 http://archive.ubuntu.com/ubuntu focal-security/main amd64 Packages And the secure channel test succeeds: PS C:\Users\focal.SAMBA.002> Test-ComputerSecureChannel -Verbose VERBOSE: Performing the operation "Test-ComputerSecureChannel" on target "DESKTOP-FN048B9". True VERBOSE: The secure channel between the local computer and the domain samba.example is in good condition. b) remote desktop Trying to connect yields this error: [17:08:55:427] [565043:565043] [WARN][com.freerdp.crypto] - The VerifyChangedCertificate callback is deprecated, migrate your application to VerifyChangedCertx [17:09:13:519] [565043:565043] [WARN][com.freerdp.core.nla] - SPNEGO received NTSTATUS: STATUS_TRUSTED_RELATIONSHIP_FAILURE [0xC000018D] from server [17:09:13:519] [565043:565043] [ERROR][com.freerdp.core.nla] - SPNEGO failed with NTSTATUS: STATUS_TRUSTED_RELATIONSHIP_FAILURE [0xC000018D] [17:09:13:519] [565043:565043] [ERROR][com.freerdp.core] - nla_recv_pdu:freerdp_set_last_error_ex ERRCONNECT_AUTHENTICATION_FAILED [0x00020009] [17:09:13:519] [565043:565043] [ERROR][com.freerdp.core.rdp] - rdp_recv_callback: CONNECTION_STATE_NLA - nla_recv_pdu() fail Then apply the update to the version in proposed: ubuntu@f-smb-ad:~$ apt-cache policy samba samba: Installed: 2:4.15.13+dfsg-0ubuntu0.20.04.4 Candidate: 2:4.15.13+dfsg-0ubuntu0.20.04.4 Version table: *** 2:4.15.13+dfsg-0ubuntu0.20.04.4 500 500 http://archive.ubuntu.com/ubuntu focal-proposed/main amd64 Packages 100 /var/lib/dpkg/status 2:4.15.13+dfsg-0ubuntu0.20.04.3 500 500 http://archive.ubuntu.com/ubuntu focal-updates/main amd64 Packages 500 http://archive.ubuntu.com/ubuntu focal-security/main amd64 Packages And the remote desktop connection this time works without issues. c) As an additional test, it turns out that a simple smbclient command would also fail with an error about trust relationship, before applying the update: ubuntu@f-smb-ad:~$ smbclient -L 192.168.100.190 -U focal Password for [SAMBA\focal]: session setup failed: NT_STATUS_TRUSTED_RELATIONSHIP_FAILURE After the update, it works: ubuntu@f-smb-ad:~$ smbclient -L 192.168.100.190 -U focal Password for [SAMBA\focal]: Sharename Type Comment --------- ---- ------- ADMIN$ Disk Remote Admin C$ Disk Default share Documents Disk IPC$ IPC Remote IPC Users Disk SMB1 disabled -- no workgroup available Focal verification succeeded.