I am using cygwin to attempt to run Ansible in windows.  We have ansible 
playbooks that will run fine when executed from a linux box.  However, when 
I attempt to connect to the servers with Ansible on Windows I get the 
following error occasionally:
SSH Error: data could not be sent to the remote host. Make sure this host 
can be reached over ssh

I initially thought there was a configuration issue.  However, I am able to 
make a successful connection occasionally. I am attaching a log that shows 
requests I made while trying to figure it out.  

Is there anyway to further diagnose this issue?

This was very frustrating because I tried literally everything I could 
think of.  I knew the entire time that my public/private key files were 
correct but I never got a successful ping unless I did the requests in 
succession.


Couldn't attach file.. so here:

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh


username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping -u username

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh


username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping -u username -k

SSH password:

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

}

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping -k

SSH password:

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh


username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping -u username -k

SSH password:

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping -u username -k

SSH password:

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping -u username -k

SSH password:

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

 

///when password was entered incorrectly

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping -u username -k

SSH password:

dns-1.prod.path | FAILED >> {

    "failed": true,

    "msg": "",

    "parsed": false

} 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping -u username -k

SSH password:

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

} 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

} 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

} 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

} 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

} 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

} 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

} 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

} 

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | FAILED => SSH Error: data could not be sent to the remote 
host. Make sure this host can be reached over ssh

username@server /cygdrive/c/SourceCode/path

$ ansible dns-1.prod.path -m ping

dns-1.prod.path | success >> {

    "changed": false,

    "ping": "pong"

}

 

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