diff --git a/RemoteFile/RemoteCertificateStore.cs b/RemoteFile/RemoteCertificateStore.cs
index 3a8dd18..ce0538f 100644
--- a/RemoteFile/RemoteCertificateStore.cs
+++ b/RemoteFile/RemoteCertificateStore.cs
@@ -454,8 +454,6 @@ internal void Initialize(string sudoImpersonatedUser)
             else
                 RemoteHandler = new WinRMHandler(Server, ServerId, ServerPassword, treatAsLocal);
 
-            RemoteHandler.Initialize();
-
             logger.MethodExit(LogLevel.Debug);
         }
 
diff --git a/RemoteFile/RemoteHandlers/BaseRemoteHandler.cs b/RemoteFile/RemoteHandlers/BaseRemoteHandler.cs
index 179e929..f8a0ca6 100644
--- a/RemoteFile/RemoteHandlers/BaseRemoteHandler.cs
+++ b/RemoteFile/RemoteHandlers/BaseRemoteHandler.cs
@@ -33,8 +33,6 @@ public static void AreLinuxPermissionsValid(string permissions)
                 throw new RemoteFileException($"Invalid format for Linux file permissions.  This value must be exactly 3 digits long with each digit between 0-7 but found {permissions} instead.");
         }
 
-        public abstract void Initialize();
-
         public abstract void Terminate();
 
         public abstract string RunCommand(string commandText, object[] arguments, bool withSudo, string[] passwordsToMaskInLog);
diff --git a/RemoteFile/RemoteHandlers/IRemoteHandler.cs b/RemoteFile/RemoteHandlers/IRemoteHandler.cs
index 34f93a9..619e3b9 100644
--- a/RemoteFile/RemoteHandlers/IRemoteHandler.cs
+++ b/RemoteFile/RemoteHandlers/IRemoteHandler.cs
@@ -13,8 +13,6 @@ namespace Keyfactor.Extensions.Orchestrator.RemoteFile.RemoteHandlers
     /// </summary>
     interface IRemoteHandler
     {
-        void Initialize();
-
         void Terminate();
 
         string RunCommand(string commandText, object[] arguments, bool withSudo, string[] passwordsToMaskInLog);
diff --git a/RemoteFile/RemoteHandlers/LinuxLocalHandler.cs b/RemoteFile/RemoteHandlers/LinuxLocalHandler.cs
index 8195ad4..f7b45ac 100644
--- a/RemoteFile/RemoteHandlers/LinuxLocalHandler.cs
+++ b/RemoteFile/RemoteHandlers/LinuxLocalHandler.cs
@@ -27,12 +27,6 @@ class LinuxLocalHandler : BaseRemoteHandler
         private Command BaseCommand { get; set; }
 
         internal LinuxLocalHandler()
-        {
-            _logger.MethodEntry(LogLevel.Debug);
-            _logger.MethodExit(LogLevel.Debug);
-        }
-
-        public override void Initialize()
         {
             _logger.MethodEntry(LogLevel.Debug);
 
diff --git a/RemoteFile/RemoteHandlers/SSHHandler.cs b/RemoteFile/RemoteHandlers/SSHHandler.cs
index ab95c5c..c21fbd3 100644
--- a/RemoteFile/RemoteHandlers/SSHHandler.cs
+++ b/RemoteFile/RemoteHandlers/SSHHandler.cs
@@ -20,6 +20,7 @@
 using Keyfactor.PKI.PEM;
 using static Microsoft.ApplicationInsights.MetricDimensionNames.TelemetryContext;
 using Renci.SshNet.Common;
+using Org.BouncyCastle.Bcpg;
 
 namespace Keyfactor.Extensions.Orchestrator.RemoteFile.RemoteHandlers
 {
@@ -28,6 +29,7 @@ class SSHHandler : BaseRemoteHandler
         private ConnectionInfo Connection { get; set; }
         private string SudoImpersonatedUser { get; set; }
         private bool IsStoreServerLinux { get; set; }
+        private string UserId { get; set; }
         private string Password { get; set; }
         private SshClient sshClient;
 
@@ -38,16 +40,25 @@ internal SSHHandler(string server, string serverLogin, string serverPassword, bo
             Server = server;
             SudoImpersonatedUser = sudoImpersonatedUser;
             IsStoreServerLinux = isStoreServerLinux;
+            UserId = serverLogin;
             Password = serverPassword;
 
-            List<AuthenticationMethod> authenticationMethods = new List<AuthenticationMethod>();
             if (serverPassword.Length < PASSWORD_LENGTH_MAX)
             {
-                authenticationMethods.Add(new PasswordAuthenticationMethod(serverLogin, serverPassword));
-
-                KeyboardInteractiveAuthenticationMethod keyboardAuthentication = new KeyboardInteractiveAuthenticationMethod(UserId);
-                keyboardAuthentication.AuthenticationPrompt += KeyboardAuthentication_AuthenticationPrompt;
-                authenticationMethods.Add(keyboardAuthentication);
+                try
+                {
+                    Connection = new ConnectionInfo(server, serverLogin, new PasswordAuthenticationMethod(serverLogin, serverPassword));
+                    SshClient tempSshClient = new SshClient(Connection);
+                    tempSshClient.Connect();
+                    tempSshClient.Disconnect();
+                    tempSshClient.Dispose();
+                }
+                catch (Exception ex)
+                {
+                    KeyboardInteractiveAuthenticationMethod keyboardAuthentication = new KeyboardInteractiveAuthenticationMethod(UserId);
+                    keyboardAuthentication.AuthenticationPrompt += KeyboardAuthentication_AuthenticationPrompt;
+                    Connection = new ConnectionInfo(server, serverLogin, keyboardAuthentication);
+                }
             }
             else
             {
@@ -68,18 +79,9 @@ internal SSHHandler(string server, string serverLogin, string serverPassword, bo
                     }
                 }
 
-                authenticationMethods.Add(new PrivateKeyAuthenticationMethod(serverLogin, privateKeyFile));
+                Connection = new ConnectionInfo(server, serverLogin, new PrivateKeyAuthenticationMethod(serverLogin, privateKeyFile)); 
             }
 
-            Connection = new ConnectionInfo(server, serverLogin, authenticationMethods.ToArray());
-
-            _logger.MethodExit(LogLevel.Debug);
-        }
-
-        public override void Initialize()
-        {
-            _logger.MethodEntry(LogLevel.Debug);
-
             try
             {
                 sshClient = new SshClient(Connection);
diff --git a/RemoteFile/RemoteHandlers/WinRMHandler.cs b/RemoteFile/RemoteHandlers/WinRMHandler.cs
index c884283..1d1a041 100644
--- a/RemoteFile/RemoteHandlers/WinRMHandler.cs
+++ b/RemoteFile/RemoteHandlers/WinRMHandler.cs
@@ -43,13 +43,6 @@ internal WinRMHandler(string server, string serverLogin, string serverPassword,
                 }
             }
 
-            _logger.MethodExit(LogLevel.Debug);
-        }
-
-        public override void Initialize()
-        {
-            _logger.MethodEntry(LogLevel.Debug);
-
             try
             {
                 if (RunLocal)
@@ -69,8 +62,8 @@ public override void Initialize()
 
             catch (Exception ex)
             {
-                _logger.LogError($"Exception during Initialize...{RemoteFileException.FlattenExceptionMessages(ex, ex.Message)}");
-                throw ex;
+                _logger.LogError($"Exception attempting to connect to server...{RemoteFileException.FlattenExceptionMessages(ex, ex.Message)}");
+                throw;
             }
 
             _logger.MethodExit(LogLevel.Debug);