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I am unable to ssh into my raspberry pi 3b+ from Windows 10. I was able to up until yesterday evening. Not sure how to troubleshoot at this point. I am able to SSH into the pi from a virtual machine running ubuntu.

I'm able to ping the pi from the windows machine and am able to ping the windows machine from the pi. PuTTY and PowerShell both report Connection timed out when attempting to ssh to the pi.

My pi is at IP 192.168.1.69 and the windows machine is at 192.168.1.80. Running ssh -vvv pi@192.168.1.69 from windows results in the following:

OpenSSH_for_Windows_7.6p1, LibreSSL 2.6.4
debug3: Failed to open file:C:\\Users\\aceda/.ssh/config error:2
debug3: Failed to open file:C:\\ProgramData\\ssh/ssh_config error:2
debug2: resolving "192.168.1.69" port 22
debug2: ssh_connect_direct: needpriv 0
debug1: Connecting to 192.168.1.69 [192.168.1.69] port 22.
debug3: finish_connect - ERROR: async io completed with error: 10060, io:0000025506CC9EC0
debug1: connect to address 192.168.1.69 port 22: Connection timed out
ssh: connect to host 192.168.1.69 port 22: Connection timed out

I searched around for help with the finish_connect - ERROR: async io completed with error: 10060 error above but couldn't find much that helped me.

I'm looking for help on how to determine what is occurring on the pi that is blocking my windows machine from connecting to it.

  • A timeout is usually an indication that a firewall is blocking the connection, or you have the wrong address. – RalfFriedl Jul 5 at 17:10
  • My pi is showing that the firewall is inactive. I have verified that I have the correct IP address. I'm also able to ssh into the pi from a virtual machine I have set up. Thanks for the ideas. – acedanger Jul 5 at 17:24
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I finally figure out what the issue was - fail2ban banned my IP.

$ sudo iptables -L f2b-sshd -v -n --line-numbers                                              [13:34:09]
Chain f2b-sshd (1 references)
num   pkts bytes target     prot opt in     out     source               destination         
1       44  2288 REJECT     all  --  *      *       192.168.1.80         0.0.0.0/0            reject-with icmp-port-unreachable

Removing that entries from iptables resolve my issue.

sudo iptables -D f2b-sshd 1 
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    You should whitelist your local network with ignoreip = 127.0.0.1/8 192.168.1.0/24 192.168.137.0/24 10.8.0.0/24 in /etc/fail2ban/jail.conf – Dougie Jul 5 at 19:31

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