diff --git a/lib/msf/base/sessions/aws_instance_connect_command_shell_bind.rb b/lib/msf/base/sessions/aws_instance_connect_command_shell_bind.rb
index 0cbd7fee5b2bb..7c8c20b0744e8 100644
--- a/lib/msf/base/sessions/aws_instance_connect_command_shell_bind.rb
+++ b/lib/msf/base/sessions/aws_instance_connect_command_shell_bind.rb
@@ -76,7 +76,7 @@ def desc
     end
 
     def bootstrap(datastore = {}, handler = nil)
-      @ssh_command_stream = Net::SSH::CommandStream.new(ssh_connection, session: self)
+      @ssh_command_stream = Net::SSH::CommandStream.new(ssh_connection, session: self, error_callback: method(:print_error))
 
       @ssh_command_stream.verify_channel
       # set remote_window_size to 32 which seems to help stability
diff --git a/lib/msf/base/sessions/ssh_command_shell_bind.rb b/lib/msf/base/sessions/ssh_command_shell_bind.rb
index 2526d6c37dd21..9a22f5e82f821 100644
--- a/lib/msf/base/sessions/ssh_command_shell_bind.rb
+++ b/lib/msf/base/sessions/ssh_command_shell_bind.rb
@@ -243,7 +243,7 @@ def bootstrap(datastore = {}, handler = nil)
       # shells accessed through SSH may respond to the echo command issued for verification as expected
       datastore['AutoVerifySession'] &= @platform.blank?
 
-      @rstream = Net::SSH::CommandStream.new(ssh_connection, session: self).lsock
+      @rstream = Net::SSH::CommandStream.new(ssh_connection, session: self, error_callback: method(:print_error)).lsock
       super
 
       @info = "SSH #{username} @ #{@peer_info}"
diff --git a/lib/net/ssh/command_stream.rb b/lib/net/ssh/command_stream.rb
index 30f6edc25040c..3c17d7376a330 100644
--- a/lib/net/ssh/command_stream.rb
+++ b/lib/net/ssh/command_stream.rb
@@ -2,7 +2,7 @@
 
 class Net::SSH::CommandStream
 
-  attr_accessor :channel, :thread, :error, :ssh, :session
+  attr_accessor :channel, :thread, :error, :ssh, :session, :error_callback
   attr_accessor :lsock, :rsock, :monitor
 
   module PeerInfo
@@ -13,7 +13,7 @@ module PeerInfo
 
   def shell_requested(channel, success)
     unless success
-      error = Net::SSH::ChannelRequestFailed, 'Shell/exec channel request failed'
+      error = Net::SSH::ChannelRequestFailed.new('Shell/exec channel request failed')
       handle_error(error: error)
       raise error
     end
@@ -42,8 +42,9 @@ def shell_requested(channel, success)
     end
   end
 
-  def initialize(ssh, cmd = nil, pty: false, cleanup: false, session: nil)
+  def initialize(ssh, cmd = nil, pty: false, cleanup: false, session: nil, error_callback: nil)
     self.session = session
+    self.error_callback = error_callback
     self.lsock, self.rsock = Rex::Socket.tcp_socket_pair()
     self.lsock.extend(Rex::IO::Stream)
     self.lsock.extend(PeerInfo)
@@ -129,6 +130,11 @@ def verify_channel
 
   def handle_error(error: nil)
     self.error = error if error
+
+    if self.error_callback
+      self.error_callback.call("SSH Command Stream encountered an error: #{self.error} (Server Version: #{self.ssh.transport.server_version.version})")
+    end
+
     cleanup
   end
 
diff --git a/modules/auxiliary/scanner/ssh/eaton_xpert_backdoor.rb b/modules/auxiliary/scanner/ssh/eaton_xpert_backdoor.rb
index 31832116bdc0f..2be96519f268c 100644
--- a/modules/auxiliary/scanner/ssh/eaton_xpert_backdoor.rb
+++ b/modules/auxiliary/scanner/ssh/eaton_xpert_backdoor.rb
@@ -84,7 +84,7 @@ def run_host(ip)
       info: version
     )
 
-    shell = Net::SSH::CommandStream.new(ssh)
+    shell = Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error))
 
     # XXX: Wait for CommandStream to log a channel request failure
     sleep 0.1
diff --git a/modules/auxiliary/scanner/ssh/fortinet_backdoor.rb b/modules/auxiliary/scanner/ssh/fortinet_backdoor.rb
index 7f874e63e9dde..8f344692675f9 100644
--- a/modules/auxiliary/scanner/ssh/fortinet_backdoor.rb
+++ b/modules/auxiliary/scanner/ssh/fortinet_backdoor.rb
@@ -77,7 +77,7 @@ def run_host(ip)
       info: version
     )
 
-    shell = Net::SSH::CommandStream.new(ssh)
+    shell = Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error))
 
     # XXX: Wait for CommandStream to log a channel request failure
     sleep 0.1
diff --git a/modules/auxiliary/scanner/ssh/libssh_auth_bypass.rb b/modules/auxiliary/scanner/ssh/libssh_auth_bypass.rb
index b5341b2b95857..2ae817c2467a5 100644
--- a/modules/auxiliary/scanner/ssh/libssh_auth_bypass.rb
+++ b/modules/auxiliary/scanner/ssh/libssh_auth_bypass.rb
@@ -120,7 +120,7 @@ def run_host(ip)
       info: version
     )
 
-    shell = Net::SSH::CommandStream.new(ssh, datastore['CMD'], pty: datastore['SPAWN_PTY'])
+    shell = Net::SSH::CommandStream.new(ssh, datastore['CMD'], pty: datastore['SPAWN_PTY'], error_callback: method(:print_error))
 
     # XXX: Wait for CommandStream to log a channel request failure
     sleep 0.1
diff --git a/modules/exploits/apple_ios/ssh/cydia_default_ssh.rb b/modules/exploits/apple_ios/ssh/cydia_default_ssh.rb
index 4ab55b0fce97e..61b5a1174fe51 100644
--- a/modules/exploits/apple_ios/ssh/cydia_default_ssh.rb
+++ b/modules/exploits/apple_ios/ssh/cydia_default_ssh.rb
@@ -110,7 +110,7 @@ def do_login(user, pass)
     end
 
     if ssh
-      conn = Net::SSH::CommandStream.new(ssh)
+      conn = Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error))
       ssh = nil
       return conn
     end
diff --git a/modules/exploits/freebsd/http/junos_phprc_auto_prepend_file.rb b/modules/exploits/freebsd/http/junos_phprc_auto_prepend_file.rb
index 6a48241c626b5..e66933717e996 100644
--- a/modules/exploits/freebsd/http/junos_phprc_auto_prepend_file.rb
+++ b/modules/exploits/freebsd/http/junos_phprc_auto_prepend_file.rb
@@ -349,7 +349,7 @@ def ssh_login
     end
 
     if ssh
-      Net::SSH::CommandStream.new(ssh)
+      Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error))
     end
   end
 
diff --git a/modules/exploits/linux/http/ubiquiti_airos_file_upload.rb b/modules/exploits/linux/http/ubiquiti_airos_file_upload.rb
index df867f0fb842a..349f6afbe8816 100644
--- a/modules/exploits/linux/http/ubiquiti_airos_file_upload.rb
+++ b/modules/exploits/linux/http/ubiquiti_airos_file_upload.rb
@@ -156,7 +156,7 @@ def ssh_login
         private: private_key,
         private_type: :ssh_key
       )
-      return Net::SSH::CommandStream.new(ssh)
+      return Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error))
     end
 
     nil
diff --git a/modules/exploits/linux/ssh/ceragon_fibeair_known_privkey.rb b/modules/exploits/linux/ssh/ceragon_fibeair_known_privkey.rb
index 116cad9e906bf..10a0c6b909141 100644
--- a/modules/exploits/linux/ssh/ceragon_fibeair_known_privkey.rb
+++ b/modules/exploits/linux/ssh/ceragon_fibeair_known_privkey.rb
@@ -111,7 +111,7 @@ def do_login(user)
     if ssh_socket
 
       # Create a new session from the socket, then dump it.
-      conn = Net::SSH::CommandStream.new(ssh_socket)
+      conn = Net::SSH::CommandStream.new(ssh_socket, error_callback: method(:print_error))
       ssh_socket = nil
 
       return conn
diff --git a/modules/exploits/linux/ssh/cisco_ucs_scpuser.rb b/modules/exploits/linux/ssh/cisco_ucs_scpuser.rb
index 539e44d1795c9..dbb72d8f1b9f8 100644
--- a/modules/exploits/linux/ssh/cisco_ucs_scpuser.rb
+++ b/modules/exploits/linux/ssh/cisco_ucs_scpuser.rb
@@ -114,7 +114,7 @@ def do_login(user, pass)
     end
 
     if ssh
-      conn = Net::SSH::CommandStream.new(ssh)
+      conn = Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error))
       ssh = nil
       return conn
     end
diff --git a/modules/exploits/linux/ssh/exagrid_known_privkey.rb b/modules/exploits/linux/ssh/exagrid_known_privkey.rb
index d4cce50196d70..6f8e064e108d8 100644
--- a/modules/exploits/linux/ssh/exagrid_known_privkey.rb
+++ b/modules/exploits/linux/ssh/exagrid_known_privkey.rb
@@ -103,7 +103,7 @@ def do_login(ssh_options)
     if ssh_socket
 
       # Create a new session from the socket, then dump it.
-      conn = Net::SSH::CommandStream.new(ssh_socket)
+      conn = Net::SSH::CommandStream.new(ssh_socket, error_callback: method(:print_error))
       ssh_socket = nil
 
       return conn
diff --git a/modules/exploits/linux/ssh/f5_bigip_known_privkey.rb b/modules/exploits/linux/ssh/f5_bigip_known_privkey.rb
index 9fabb88999cef..84d8829b00447 100644
--- a/modules/exploits/linux/ssh/f5_bigip_known_privkey.rb
+++ b/modules/exploits/linux/ssh/f5_bigip_known_privkey.rb
@@ -110,7 +110,7 @@ def do_login(user)
     return false unless ssh_socket
 
     # Create a new session from the socket, then dump it.
-    conn = Net::SSH::CommandStream.new(ssh_socket)
+    conn = Net::SSH::CommandStream.new(ssh_socket, error_callback: method(:print_error))
     ssh_socket = nil
     conn
   end
diff --git a/modules/exploits/linux/ssh/ibm_drm_a3user.rb b/modules/exploits/linux/ssh/ibm_drm_a3user.rb
index f011ef9d17ef1..9e46e65fc1992 100644
--- a/modules/exploits/linux/ssh/ibm_drm_a3user.rb
+++ b/modules/exploits/linux/ssh/ibm_drm_a3user.rb
@@ -113,7 +113,7 @@ def do_login(user, pass)
       fail_with(Failure::Unknown, "#{peer} SSH Error: #{e.class} : #{e.message}")
     end
 
-    return Net::SSH::CommandStream.new(ssh) if ssh
+    return Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error)) if ssh
 
     nil
   end
diff --git a/modules/exploits/linux/ssh/loadbalancerorg_enterprise_known_privkey.rb b/modules/exploits/linux/ssh/loadbalancerorg_enterprise_known_privkey.rb
index 750e4cb387d18..e3cc9f49019ae 100644
--- a/modules/exploits/linux/ssh/loadbalancerorg_enterprise_known_privkey.rb
+++ b/modules/exploits/linux/ssh/loadbalancerorg_enterprise_known_privkey.rb
@@ -108,7 +108,7 @@ def do_login(user)
     if ssh_socket
 
       # Create a new session from the socket, then dump it.
-      conn = Net::SSH::CommandStream.new(ssh_socket)
+      conn = Net::SSH::CommandStream.new(ssh_socket, error_callback: method(:print_error))
       ssh_socket = nil
 
       return conn
diff --git a/modules/exploits/linux/ssh/microfocus_obr_shrboadmin.rb b/modules/exploits/linux/ssh/microfocus_obr_shrboadmin.rb
index f12ce10a97fbd..d765d41116e39 100644
--- a/modules/exploits/linux/ssh/microfocus_obr_shrboadmin.rb
+++ b/modules/exploits/linux/ssh/microfocus_obr_shrboadmin.rb
@@ -113,7 +113,7 @@ def do_login(user, pass)
     end
 
     if ssh
-      conn = Net::SSH::CommandStream.new(ssh)
+      conn = Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error))
       ssh = nil
       return conn
     end
diff --git a/modules/exploits/linux/ssh/quantum_dxi_known_privkey.rb b/modules/exploits/linux/ssh/quantum_dxi_known_privkey.rb
index ce79add91200e..39a445697357e 100644
--- a/modules/exploits/linux/ssh/quantum_dxi_known_privkey.rb
+++ b/modules/exploits/linux/ssh/quantum_dxi_known_privkey.rb
@@ -107,7 +107,7 @@ def do_login(user)
     if ssh_socket
 
       # Create a new session from the socket, then dump it.
-      conn = Net::SSH::CommandStream.new(ssh_socket)
+      conn = Net::SSH::CommandStream.new(ssh_socket, error_callback: method(:print_error))
       ssh_socket = nil
 
       return conn
diff --git a/modules/exploits/linux/ssh/quantum_vmpro_backdoor.rb b/modules/exploits/linux/ssh/quantum_vmpro_backdoor.rb
index ac2a5674a3606..b37a5b38335f0 100644
--- a/modules/exploits/linux/ssh/quantum_vmpro_backdoor.rb
+++ b/modules/exploits/linux/ssh/quantum_vmpro_backdoor.rb
@@ -110,7 +110,7 @@ def do_login(user, pass)
     end
 
     if ssh
-      conn = Net::SSH::CommandStream.new(ssh, 'shell-escape')
+      conn = Net::SSH::CommandStream.new(ssh, 'shell-escape', error_callback: method(:print_error))
       return conn
     end
 
diff --git a/modules/exploits/linux/ssh/symantec_smg_ssh.rb b/modules/exploits/linux/ssh/symantec_smg_ssh.rb
index 8c7f32067c284..638b0e1d1394c 100644
--- a/modules/exploits/linux/ssh/symantec_smg_ssh.rb
+++ b/modules/exploits/linux/ssh/symantec_smg_ssh.rb
@@ -100,7 +100,7 @@ def do_login(user, pass)
     end
 
     if ssh
-      conn = Net::SSH::CommandStream.new(ssh)
+      conn = Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error))
       ssh = nil
       return conn
     end
diff --git a/modules/exploits/linux/ssh/vmware_vdp_known_privkey.rb b/modules/exploits/linux/ssh/vmware_vdp_known_privkey.rb
index e1b41727d0700..3faf750d639a5 100644
--- a/modules/exploits/linux/ssh/vmware_vdp_known_privkey.rb
+++ b/modules/exploits/linux/ssh/vmware_vdp_known_privkey.rb
@@ -104,7 +104,7 @@ def do_login
     if ssh_socket
 
       # Create a new session from the socket, then dump it.
-      conn = Net::SSH::CommandStream.new(ssh_socket)
+      conn = Net::SSH::CommandStream.new(ssh_socket, error_callback: method(:print_error))
       sockets.delete(ssh_socket.transport.socket)
 
       return conn
diff --git a/modules/exploits/linux/ssh/vmware_vrni_known_privkey.rb b/modules/exploits/linux/ssh/vmware_vrni_known_privkey.rb
index c2443ab3bbb4f..821433c053d38 100644
--- a/modules/exploits/linux/ssh/vmware_vrni_known_privkey.rb
+++ b/modules/exploits/linux/ssh/vmware_vrni_known_privkey.rb
@@ -141,7 +141,7 @@ def do_login(user, key_data)
 
     if ssh_socket
       # Create a new session from the socket, then close it.
-      conn = Net::SSH::CommandStream.new(ssh_socket)
+      conn = Net::SSH::CommandStream.new(ssh_socket, error_callback: method(:print_error))
       ssh_socket = nil
 
       return conn
diff --git a/modules/exploits/unix/http/schneider_electric_net55xx_encoder.rb b/modules/exploits/unix/http/schneider_electric_net55xx_encoder.rb
index a26bf80f64248..22e99cd1e739b 100644
--- a/modules/exploits/unix/http/schneider_electric_net55xx_encoder.rb
+++ b/modules/exploits/unix/http/schneider_electric_net55xx_encoder.rb
@@ -141,7 +141,7 @@ def do_login
       print_error "#{rhost}:22 SSH Error: #{e.class} : #{e.message}"
     end
     if ssh
-      conn = Net::SSH::CommandStream.new(ssh)
+      conn = Net::SSH::CommandStream.new(ssh, error_callback: method(:print_error))
       return conn
     end
   end
diff --git a/modules/exploits/unix/ssh/array_vxag_vapv_privkey_privesc.rb b/modules/exploits/unix/ssh/array_vxag_vapv_privkey_privesc.rb
index 078f2a61534ff..acee07511ead0 100644
--- a/modules/exploits/unix/ssh/array_vxag_vapv_privkey_privesc.rb
+++ b/modules/exploits/unix/ssh/array_vxag_vapv_privkey_privesc.rb
@@ -181,6 +181,6 @@ def exploit
 
     # Make the SSH connection and execute our commands + payload
     print_status("#{rhost}:#{rport} - Sending and executing payload to gain root privileges!")
-    Net::SSH::CommandStream.new(ssh, build_command)
+    Net::SSH::CommandStream.new(ssh, build_command, error_callback: method(:print_error))
   end
 end
diff --git a/modules/exploits/unix/ssh/tectia_passwd_changereq.rb b/modules/exploits/unix/ssh/tectia_passwd_changereq.rb
index b08c4861e45a5..31b0824eb01c8 100644
--- a/modules/exploits/unix/ssh/tectia_passwd_changereq.rb
+++ b/modules/exploits/unix/ssh/tectia_passwd_changereq.rb
@@ -179,7 +179,7 @@ def userauth_passwd_change(user, transport, connection)
       message = transport.next_message.type
 
       if message.to_i == 6 #SSH2_MSG_SERVICE_ACCEPT
-        shell = Net::SSH::CommandStream.new(connection)
+        shell = Net::SSH::CommandStream.new(connection, error_callback: method(:print_error))
         connection = nil
         return shell
       end