diff --git a/cmd/podman/root.go b/cmd/podman/root.go
index 2aa7267c28..dd9c75ecee 100644
--- a/cmd/podman/root.go
+++ b/cmd/podman/root.go
@@ -290,6 +290,7 @@ func resolveDestination() (string, string) {
 
 	cfg, err := config.ReadCustomConfig()
 	if err != nil {
+		logrus.Warning(errors.Wrap(err, "unable to read local containers.conf"))
 		return registry.DefaultAPIAddress(), ""
 	}
 
diff --git a/cmd/podman/system/connection/add.go b/cmd/podman/system/connection/add.go
index 89cea10ca6..af13b970cc 100644
--- a/cmd/podman/system/connection/add.go
+++ b/cmd/podman/system/connection/add.go
@@ -124,6 +124,7 @@ func add(cmd *cobra.Command, args []string) error {
 		cfg.Engine.ServiceDestinations = map[string]config.Destination{
 			args[0]: dst,
 		}
+		cfg.Engine.ActiveService = args[0]
 	} else {
 		cfg.Engine.ServiceDestinations[args[0]] = dst
 	}
@@ -181,12 +182,20 @@ func getUDS(cmd *cobra.Command, uri *url.URL) (string, error) {
 		authMethods = append(authMethods, ssh.PublicKeysCallback(a.Signers))
 	}
 
-	config := &ssh.ClientConfig{
+	if len(authMethods) == 0 {
+		pass, err := terminal.ReadPassword(fmt.Sprintf("%s's login password:", uri.User.Username()))
+		if err != nil {
+			return "", err
+		}
+		authMethods = append(authMethods, ssh.Password(string(pass)))
+	}
+
+	cfg := &ssh.ClientConfig{
 		User:            uri.User.Username(),
 		Auth:            authMethods,
 		HostKeyCallback: ssh.InsecureIgnoreHostKey(),
 	}
-	dial, err := ssh.Dial("tcp", uri.Host, config)
+	dial, err := ssh.Dial("tcp", uri.Host, cfg)
 	if err != nil {
 		return "", errors.Wrapf(err, "failed to connect to %q", uri.Host)
 	}
diff --git a/contrib/msi/podman.wxs b/contrib/msi/podman.wxs
index c2c2cea4f2..ff8160a535 100644
--- a/contrib/msi/podman.wxs
+++ b/contrib/msi/podman.wxs
@@ -24,8 +24,7 @@
               <CreateFolder/>
             </Component>
             <Component Id="MainExecutable" Guid="73752F94-6589-4C7B-ABED-39D655A19714">
-              <File Id="520C6E17-77A2-4F41-9611-30FA763A0702" Name="podman-remote-windows.exe" Source="bin/podman-remote-windows.exe"/>
-              <File Id="A14218A0-4180-44AC-B109-7C63B3099DCA" Name="podman.bat" Source="podman.bat" KeyPath="yes"/>
+              <File Id="520C6E17-77A2-4F41-9611-30FA763A0702" Name="podman.exe" Source="bin/podman-remote-windows.exe" KeyPath="yes"/>
             </Component>
           </Directory>
         </Directory>
@@ -33,7 +32,7 @@
     </Directory>
 
     <Property Id="setx" Value="setx.exe"/>
-    <CustomAction Id="ChangePath" ExeCommand="PATH &quot;%PATH%;[INSTALLDIR] &quot;" Property="setx" Execute="deferred" Impersonate="yes" Return="check"/>
+    <CustomAction Id="ChangePath" ExeCommand="PATH &quot;%PATH%;[INSTALLDIR]&quot;" Property="setx" Execute="deferred" Impersonate="yes" Return="check"/>
 
     <Feature Id="Complete" Level="1">
       <ComponentRef Id="INSTALLDIR_Component"/>
diff --git a/pkg/bindings/connection.go b/pkg/bindings/connection.go
index e820e1c8b3..ef9644de8e 100644
--- a/pkg/bindings/connection.go
+++ b/pkg/bindings/connection.go
@@ -180,8 +180,9 @@ func pingNewConnection(ctx context.Context) error {
 }
 
 func sshClient(_url *url.URL, secure bool, passPhrase string, identity string) (Connection, error) {
+	// if you modify the authmethods or their conditionals, you will also need to make similar
+	// changes in the client (currently cmd/podman/system/connection/add getUDS).
 	authMethods := []ssh.AuthMethod{}
-
 	if len(identity) > 0 {
 		auth, err := terminal.PublicKey(identity, []byte(passPhrase))
 		if err != nil {
@@ -205,6 +206,13 @@ func sshClient(_url *url.URL, secure bool, passPhrase string, identity string) (
 	if pw, found := _url.User.Password(); found {
 		authMethods = append(authMethods, ssh.Password(pw))
 	}
+	if len(authMethods) == 0 {
+		pass, err := terminal.ReadPassword("Login password:")
+		if err != nil {
+			return Connection{}, err
+		}
+		authMethods = append(authMethods, ssh.Password(string(pass)))
+	}
 
 	callback := ssh.InsecureIgnoreHostKey()
 	if secure {