Delay Connecting from Ubuntu

Troubleshooting steps
https://github.com/PowerShell/Win32-OpenSSH/wiki/Troubleshooting-Steps

Terminal issue? please go through wiki
https://github.com/PowerShell/Win32-OpenSSH/wiki/TTY-PTY-support-in-Windows-OpenSSH

Please answer the following

"OpenSSH for Windows" version
((Get-Item (Get-Command sshd).Source).VersionInfo.FileVersion)
Command doesn't work but it's 8.0.0 (I downloaded today)

Server OperatingSystem
((Get-ItemProperty "HKLM:\SOFTWARE\Microsoft\Windows nt\CurrentVersion\" -Name ProductName).ProductName)
Windows 7 Professional

Client OperatingSystem
Ubuntu 14.04 LTS (Trusty)

What is failing
Connecting from Ubuntu LTS trusy, the connection is very often pausing at...
debug1: Enabling compatibility mode for protocol 2.0
debug1: Local version string SSH-2.0-OpenSSH_6.6.1p1 Ubuntu-2ubuntu2.10

Then continues quickly from this line
debug1: Remote protocol version 2.0, remote software version OpenSSH_for_Windows_8.0

The strange thing is, if I restart the service, I can connect quickly a number of times (in this case 2) and then it will start delaying again

Server Log:
5628 2019-07-03 13:23:52.152 debug1: do_cleanup
2468 2019-07-03 13:24:40.578 debug1: inetd sockets after dupping: 4, 4
2468 2019-07-03 13:24:40.578 Connection from 10.X.X port 38317 on 10.X.X port 22
2468 2019-07-03 13:24:40.578 debug1: Local version string SSH-2.0-OpenSSH_for_Windows_8.0
2468 2019-07-03 13:24:40.578 debug1: Remote protocol version 2.0, remote software version OpenSSH_6.6.1p1 Ubuntu-2ubuntu2.10
2468 2019-07-03 13:24:40.578 debug1: match: OpenSSH_6.6.1p1 Ubuntu-2ubuntu2.10 pat OpenSSH_6.6.1* compat 0x04000002
2468 2019-07-03 13:24:40.672 debug1: list_hostkey_types: rsa-sha2-512,rsa-sha2-256,ssh-rsa,ecdsa-sha2-nistp256,ssh-ed25519 [preauth]
2468 2019-07-03 13:24:40.672 debug1: SSH2_MSG_KEXINIT sent [preauth]
2468 2019-07-03 13:24:40.672 debug1: SSH2_MSG_KEXINIT received [preauth]
2468 2019-07-03 13:24:40.672 debug1: kex: algorithm: curve25519-sha256@libssh.org [preauth]
2468 2019-07-03 13:24:40.672 debug1: kex: host key algorithm: ecdsa-sha2-nistp256 [preauth]
2468 2019-07-03 13:24:40.672 debug1: kex: client->server cipher: aes128-ctr MAC: hmac-sha1-etm@openssh.com compression: none [preauth]
2468 2019-07-03 13:24:40.672 debug1: kex: server->client cipher: aes128-ctr MAC: hmac-sha1-etm@openssh.com compression: none [preauth]
2468 2019-07-03 13:24:40.672 debug1: expecting SSH2_MSG_KEX_ECDH_INIT [preauth]
2468 2019-07-03 13:24:40.678 debug1: rekey out after 4294967296 blocks [preauth]
2468 2019-07-03 13:24:40.678 debug1: SSH2_MSG_NEWKEYS sent [preauth]
2468 2019-07-03 13:24:40.678 debug1: expecting SSH2_MSG_NEWKEYS [preauth]
2468 2019-07-03 13:24:40.682 debug1: SSH2_MSG_NEWKEYS received [preauth]
2468 2019-07-03 13:24:40.682 debug1: rekey in after 4294967296 blocks [preauth]
2468 2019-07-03 13:24:40.682 debug1: KEX done [preauth]
2468 2019-07-03 13:24:40.888 debug1: userauth-request for user administrator service ssh-connection method none [preauth]
2468 2019-07-03 13:24:40.888 debug1: attempt 0 failures 0 [preauth]
2468 2019-07-03 13:24:40.890 debug1: user administrator matched group list administrators at line 87
2468 2019-07-03 13:24:40.895 debug1: userauth-request for user administrator service ssh-connection method publickey [preauth]
2468 2019-07-03 13:24:40.895 debug1: attempt 1 failures 0 [preauth]
2468 2019-07-03 13:24:40.895 debug1: userauth_pubkey: test pkalg ssh-rsa pkblob RSA SHA256:V3HXXXXXXXXXX [preauth]
2468 2019-07-03 13:24:40.895 debug1: trying public key file PROGRAMDATA/ssh/administrators_authorized_keys
2468 2019-07-03 13:24:40.895 debug1: PROGRAMDATA/ssh/administrators_authorized_keys:1: matching key found: RSA SHA256:V3HeTAXXXXXXXXX
2468 2019-07-03 13:24:40.896 debug1: PROGRAMDATA/ssh/administrators_authorized_keys:1: key options: agent-forwarding port-forwarding pty user-rc x11-forwarding
2468 2019-07-03 13:24:40.896 Accepted key RSA SHA256:V3XXXXXXX found at PROGRAMDATA/ssh/administrators_authorized_keys:1
2468 2019-07-03 13:24:40.902 Postponed publickey for administrator from 10.X.X port 38317 ssh2 [preauth]
2468 2019-07-03 13:24:40.902 debug1: userauth-request for user administrator service ssh-connection method publickey [preauth]
2468 2019-07-03 13:24:40.902 debug1: attempt 2 failures 0 [preauth]
2468 2019-07-03 13:24:40.902 debug1: trying public key file PROGRAMDATA/ssh/administrators_authorized_keys
2468 2019-07-03 13:24:40.902 debug1: PROGRAMDATA/ssh/administrators_authorized_keys:1: matching key found: RSA SHA256:V3XXXXXXX
2468 2019-07-03 13:24:40.902 debug1: PROGRAMDATA/ssh/administrators_authorized_keys:1: key options: agent-forwarding port-forwarding pty user-rc x11-forwarding
2468 2019-07-03 13:24:40.902 Accepted key RSA SHA256:V3XXXXXfound at PROGRAMDATA/ssh/administrators_authorized_keys:1
2468 2019-07-03 13:24:40.902 debug1: auth_activate_options: setting new authentication options
2468 2019-07-03 13:24:40.902 Accepted publickey for administrator from 10.X.X port 38317 ssh2: RSA SHA256:V3XXXXX
2468 2019-07-03 13:24:40.903 debug1: monitor_child_preauth: administrator has been authenticated by privileged process
2468 2019-07-03 13:24:40.909 debug1: auth_activate_options: setting new authentication options [preauth]
2468 2019-07-03 13:24:40.910 debug1: monitor_read_log: child log fd closed
2468 2019-07-03 13:24:40.926 User child is on pid 9012
9012 2019-07-03 13:24:40.971 debug1: user administrator matched group list administrators at line 87
9012 2019-07-03 13:24:40.972 debug1: rekey in after 4294967296 blocks
9012 2019-07-03 13:24:40.972 debug1: rekey out after 4294967296 blocks
9012 2019-07-03 13:24:40.972 debug1: ssh_packet_set_postauth: called
9012 2019-07-03 13:24:40.972 debug1: active: key options: agent-forwarding port-forwarding pty user-rc x11-forwarding
9012 2019-07-03 13:24:40.972 debug1: Entering interactive session for SSH2.
9012 2019-07-03 13:24:40.972 debug1: server_init_dispatch
9012 2019-07-03 13:24:40.972 debug1: server_input_channel_open: ctype session rchan 0 win 2097152 max 32768
9012 2019-07-03 13:24:40.972 debug1: input_session_request
9012 2019-07-03 13:24:40.972 debug1: channel 0: new [server-session]
9012 2019-07-03 13:24:40.972 debug1: session_new: session 0
9012 2019-07-03 13:24:40.972 debug1: session_open: channel 0
9012 2019-07-03 13:24:40.972 debug1: session_open: session 0: link with channel 0
9012 2019-07-03 13:24:40.972 debug1: server_input_channel_open: confirm session
9012 2019-07-03 13:24:40.972 debug1: server_input_global_request: rtype no-more-sessions@openssh.com want_reply 0
9012 2019-07-03 13:24:41.012 debug1: server_input_channel_req: channel 0 request env reply 0
9012 2019-07-03 13:24:41.013 debug1: session_by_channel: session 0 channel 0
9012 2019-07-03 13:24:41.013 debug1: session_input_channel_req: session 0 req env
9012 2019-07-03 13:24:41.013 debug1: server_input_channel_req: channel 0 request exec reply 1
9012 2019-07-03 13:24:41.013 debug1: session_by_channel: session 0 channel 0
9012 2019-07-03 13:24:41.013 debug1: session_input_channel_req: session 0 req exec
9012 2019-07-03 13:24:41.013 Starting session: command for administrator from 10.194.105.36 port 38317 id 0
9012 2019-07-03 13:24:41.055 debug1: Received SIGCHLD.
9012 2019-07-03 13:24:41.055 debug1: session_by_pid: pid 9760
9012 2019-07-03 13:24:41.055 debug1: session_exit_message: session 0 channel 0 pid 9760
9012 2019-07-03 13:24:41.055 debug1: session_exit_message: release channel 0
9012 2019-07-03 13:24:41.056 debug1: session_by_channel: session 0 channel 0
9012 2019-07-03 13:24:41.056 debug1: session_close_by_channel: channel 0 child 0
9012 2019-07-03 13:24:41.056 Close session: user administrator from 10.X.X port 38317 id 0
9012 2019-07-03 13:24:41.056 debug1: channel 0: free: server-session, nchannels 1
9012 2019-07-03 13:24:41.056 Received disconnect from 10.X.X port 38317:11: disconnected by user
9012 2019-07-03 13:24:41.056 Disconnected from 10.X.X port 38317
9012 2019-07-03 13:24:41.056 debug1: do_cleanup
2468 2019-07-03 13:24:41.057 debug1: do_cleanup

Start with the linked Troubleshooting Steps and TTY/PTY support wiki pages, then reproduce the intermittent delay using the Ubuntu 14.04 client and Windows 7 server while comparing the supplied client and server logs. Done means the cause of the post-restart delay is identified and a specific fix or documented workaround is validated.