https://bugzilla.mindrot.org/show_bug.cgi?id=3453

            Bug ID: 3453
           Summary: User override in Host not respected
           Product: Portable OpenSSH
           Version: 8.6p1
          Hardware: amd64
                OS: Mac OS X
            Status: NEW
          Severity: minor
          Priority: P5
         Component: ssh
          Assignee: unassigned-b...@mindrot.org
          Reporter: mattfleming...@gmail.com

Hello,

It seems that the User directive isn't resolved correctly inside a Host
anymore. Example below - note ssh is using matthewfl not matt.fleming
as configured. This was working fine with a previous version. It works
correctly if the top level User is removed.

# ~/.ssh/config

#
https://www.qualys.com/2016/01/14/cve-2016-0777-cve-2016-0778/openssh-cve-2016-0777-cve-2016-0778.txt
UseRoaming no

Compression yes

User matthewfl

Host aws-bastion
    User matt.fleming
    Hostname 54.252.158.21

Host dev-*
    User matt.fleming
    ProxyJump matt.fleming@54.252.158.21

Host dev-ssw
    HostName 172.22.5.60
    User matt.fleming

❰matthew❙~/.ssh❱✔≻ ssh dev-ssw
matthewfl@172.22.5.60: Permission denied
(publickey,gssapi-keyex,gssapi-with-mic).
❰matthew❙~/.ssh❱✘≻ ssh aws-bastion
matthewfl@54.252.158.21: Permission denied
(publickey,gssapi-keyex,gssapi-with-mic).

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