diff --git a/pkg/config/config.go b/pkg/config/config.go
index 858f961b6..cde7cec53 100644
--- a/pkg/config/config.go
+++ b/pkg/config/config.go
@@ -613,6 +613,9 @@ type Destination struct {
 
 	// Identity file with ssh key, optional
 	Identity string `toml:"identity,omitempty"`
+
+	// isMachine describes if the remote destination is a machine.
+	IsMachine bool `toml:"is_machine,omitempty"`
 }
 
 // NewConfig creates a new Config. It starts with an empty config and, if
@@ -1235,32 +1238,32 @@ func Reload() (*Config, error) {
 	return defConfig()
 }
 
-func (c *Config) ActiveDestination() (uri, identity string, err error) {
+func (c *Config) ActiveDestination() (uri, identity string, machine bool, err error) {
 	if uri, found := os.LookupEnv("CONTAINER_HOST"); found {
 		if v, found := os.LookupEnv("CONTAINER_SSHKEY"); found {
 			identity = v
 		}
-		return uri, identity, nil
+		return uri, identity, false, nil
 	}
 	connEnv := os.Getenv("CONTAINER_CONNECTION")
 	switch {
 	case connEnv != "":
 		d, found := c.Engine.ServiceDestinations[connEnv]
 		if !found {
-			return "", "", fmt.Errorf("environment variable CONTAINER_CONNECTION=%q service destination not found", connEnv)
+			return "", "", false, fmt.Errorf("environment variable CONTAINER_CONNECTION=%q service destination not found", connEnv)
 		}
-		return d.URI, d.Identity, nil
+		return d.URI, d.Identity, d.IsMachine, nil
 
 	case c.Engine.ActiveService != "":
 		d, found := c.Engine.ServiceDestinations[c.Engine.ActiveService]
 		if !found {
-			return "", "", fmt.Errorf("%q service destination not found", c.Engine.ActiveService)
+			return "", "", false, fmt.Errorf("%q service destination not found", c.Engine.ActiveService)
 		}
-		return d.URI, d.Identity, nil
+		return d.URI, d.Identity, d.IsMachine, nil
 	case c.Engine.RemoteURI != "":
-		return c.Engine.RemoteURI, c.Engine.RemoteIdentity, nil
+		return c.Engine.RemoteURI, c.Engine.RemoteIdentity, false, nil
 	}
-	return "", "", errors.New("no service destination configured")
+	return "", "", false, errors.New("no service destination configured")
 }
 
 var (
diff --git a/pkg/config/config_test.go b/pkg/config/config_test.go
index 9a13981b1..923beaf30 100644
--- a/pkg/config/config_test.go
+++ b/pkg/config/config_test.go
@@ -588,9 +588,10 @@ image_copy_tmp_dir="storage"`
 			cfg, err = ReadCustomConfig()
 			gomega.Expect(err).ShouldNot(gomega.HaveOccurred())
 
-			u, i, err := cfg.ActiveDestination()
+			u, i, m, err := cfg.ActiveDestination()
 			gomega.Expect(err).ShouldNot(gomega.HaveOccurred())
 
+			gomega.Expect(m).To(gomega.Equal(false))
 			gomega.Expect(u).To(gomega.Equal("https://qa/run/podman/podman.sock"))
 			gomega.Expect(i).To(gomega.Equal("/.ssh/id_rsa"))
 		})
@@ -620,7 +621,7 @@ image_copy_tmp_dir="storage"`
 			oldContainerConnection, hostEnvSet := os.LookupEnv("CONTAINER_CONNECTION")
 			os.Setenv("CONTAINER_CONNECTION", "QB")
 
-			u, i, err := cfg.ActiveDestination()
+			u, i, m, err := cfg.ActiveDestination()
 			// Undo that
 			if hostEnvSet {
 				os.Setenv("CONTAINER_CONNECTION", oldContainerConnection)
@@ -628,6 +629,7 @@ image_copy_tmp_dir="storage"`
 				os.Unsetenv("CONTAINER_CONNECTION")
 			}
 			gomega.Expect(err).ShouldNot(gomega.HaveOccurred())
+			gomega.Expect(m).To(gomega.Equal(false))
 
 			gomega.Expect(u).To(gomega.Equal("https://qb/run/podman/podman.sock"))
 			gomega.Expect(i).To(gomega.Equal("/.ssh/qb_id_rsa"))
@@ -660,7 +662,8 @@ image_copy_tmp_dir="storage"`
 			os.Setenv("CONTAINER_HOST", "foo.bar")
 			os.Setenv("CONTAINER_SSHKEY", "/.ssh/newid_rsa")
 
-			u, i, err := cfg.ActiveDestination()
+			u, i, m, err := cfg.ActiveDestination()
+
 			// Undo that
 			if hostEnvSet {
 				os.Setenv("CONTAINER_HOST", oldContainerHost)
@@ -675,6 +678,7 @@ image_copy_tmp_dir="storage"`
 			}
 
 			gomega.Expect(err).ShouldNot(gomega.HaveOccurred())
+			gomega.Expect(m).To(gomega.Equal(false))
 
 			gomega.Expect(u).To(gomega.Equal("foo.bar"))
 			gomega.Expect(i).To(gomega.Equal("/.ssh/newid_rsa"))
@@ -684,7 +688,7 @@ image_copy_tmp_dir="storage"`
 			cfg, err := ReadCustomConfig()
 			gomega.Expect(err).ShouldNot(gomega.HaveOccurred())
 
-			_, _, err = cfg.ActiveDestination()
+			_, _, _, err = cfg.ActiveDestination()
 			gomega.Expect(err).Should(gomega.HaveOccurred())
 		})
 
diff --git a/pkg/ssh/connection_golang.go b/pkg/ssh/connection_golang.go
index a5c1be89c..8ec3c45ed 100644
--- a/pkg/ssh/connection_golang.go
+++ b/pkg/ssh/connection_golang.go
@@ -3,6 +3,7 @@ package ssh
 import (
 	"bytes"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"io"
 	"net"
@@ -70,7 +71,7 @@ func golangConnectionDial(options ConnectionDialOptions) (*ConnectionDialReport,
 	if err != nil {
 		return nil, err
 	}
-	cfg, err := ValidateAndConfigure(uri, options.Identity)
+	cfg, err := ValidateAndConfigure(uri, options.Identity, options.InsecureIsMachineConnection)
 	if err != nil {
 		return nil, err
 	}
@@ -84,12 +85,15 @@ func golangConnectionDial(options ConnectionDialOptions) (*ConnectionDialReport,
 }
 
 func golangConnectionExec(options ConnectionExecOptions) (*ConnectionExecReport, error) {
+	if !strings.HasPrefix(options.Host, "ssh://") {
+		options.Host = "ssh://" + options.Host
+	}
 	_, uri, err := Validate(options.User, options.Host, options.Port, options.Identity)
 	if err != nil {
 		return nil, err
 	}
 
-	cfg, err := ValidateAndConfigure(uri, options.Identity)
+	cfg, err := ValidateAndConfigure(uri, options.Identity, false)
 	if err != nil {
 		return nil, err
 	}
@@ -111,11 +115,15 @@ func golangConnectionScp(options ConnectionScpOptions) (*ConnectionScpReport, er
 		return nil, err
 	}
 
+	// removed for parsing
+	if !strings.HasPrefix(host, "ssh://") {
+		host = "ssh://" + host
+	}
 	_, uri, err := Validate(options.User, host, options.Port, options.Identity)
 	if err != nil {
 		return nil, err
 	}
-	cfg, err := ValidateAndConfigure(uri, options.Identity)
+	cfg, err := ValidateAndConfigure(uri, options.Identity, false)
 	if err != nil {
 		return nil, err
 	}
@@ -209,7 +217,7 @@ func GetUserInfo(uri *url.URL) (*url.Userinfo, error) {
 // ValidateAndConfigure will take a ssh url and an identity key (rsa and the like) and ensure the information given is valid
 // iden iden can be blank to mean no identity key
 // once the function validates the information it creates and returns an ssh.ClientConfig.
-func ValidateAndConfigure(uri *url.URL, iden string) (*ssh.ClientConfig, error) {
+func ValidateAndConfigure(uri *url.URL, iden string, insecureIsMachineConnection bool) (*ssh.ClientConfig, error) {
 	var signers []ssh.Signer
 	passwd, passwdSet := uri.User.Password()
 	if iden != "" { // iden might be blank if coming from image scp or if no validation is needed
@@ -272,23 +280,61 @@ func ValidateAndConfigure(uri *url.URL, iden string) (*ssh.ClientConfig, error)
 	if err != nil {
 		return nil, err
 	}
-	keyFilePath := filepath.Join(homedir.Get(), ".ssh", "known_hosts")
-	known, err := knownhosts.New(keyFilePath)
-	if err != nil {
-		return nil, fmt.Errorf("creating host key callback function for %s: %w", keyFilePath, err)
+
+	var callback ssh.HostKeyCallback
+	if insecureIsMachineConnection {
+		callback = ssh.InsecureIgnoreHostKey()
+	} else {
+		callback = ssh.HostKeyCallback(func(host string, remote net.Addr, pubKey ssh.PublicKey) error {
+			keyFilePath := filepath.Join(homedir.Get(), ".ssh", "known_hosts")
+			known, err := knownhosts.New(keyFilePath)
+			if err != nil {
+				if errors.Is(err, os.ErrNotExist) {
+					logrus.Warn("please create a known_hosts file. The next time this host is connected to, podman will add it to known_hosts")
+					return nil
+				}
+				return err
+			}
+			// we need to check if there is an error from reading known hosts for this public key and if there is an error, what is it, and why is it happening?
+			// if it is a key mismatch we want to error since we know the host using another key
+			// however, if it is a general error not because of a known key, we want to add our key to the known_hosts file
+			hErr := known(host, remote, pubKey)
+			var keyErr *knownhosts.KeyError
+			// if keyErr.Want is not empty, we are receiving a different key meaning the host is known but we are using the wrong key
+			as := errors.As(hErr, &keyErr)
+			switch {
+			case as && len(keyErr.Want) > 0:
+				logrus.Warnf("ssh host key mismatch for host %s, got key %s of type %s", host, ssh.FingerprintSHA256(pubKey), pubKey.Type())
+				return keyErr
+			// if keyErr.Want is empty that just means we do not know this host yet, add it.
+			case as && len(keyErr.Want) == 0:
+				// write to known_hosts
+				err := addKnownHostsEntry(host, pubKey)
+				if err != nil {
+					if os.IsNotExist(err) {
+						logrus.Warn("podman will soon require a known_hosts file to function properly.")
+						return nil
+					}
+					return err
+				}
+			case hErr != nil:
+				return hErr
+			}
+			return nil
+		})
 	}
 
 	cfg := &ssh.ClientConfig{
 		User:            uri.User.Username(),
 		Auth:            authMethods,
-		HostKeyCallback: known,
+		HostKeyCallback: callback,
 		Timeout:         tick,
 	}
 	return cfg, nil
 }
 
 func getUDS(uri *url.URL, iden string) (string, error) {
-	cfg, err := ValidateAndConfigure(uri, iden)
+	cfg, err := ValidateAndConfigure(uri, iden, false)
 	if err != nil {
 		return "", fmt.Errorf("failed to validate: %w", err)
 	}
@@ -324,3 +370,20 @@ func getUDS(uri *url.URL, iden string) (string, error) {
 	}
 	return info.Host.RemoteSocket.Path, nil
 }
+
+// addKnownHostsEntry adds (host, pubKey) to user’s known_hosts.
+func addKnownHostsEntry(host string, pubKey ssh.PublicKey) error {
+	hd := homedir.Get()
+	known := filepath.Join(hd, ".ssh", "known_hosts")
+	f, err := os.OpenFile(known, os.O_APPEND|os.O_WRONLY, 0o600)
+	if err != nil {
+		return err
+	}
+	defer f.Close()
+	l := knownhosts.Line([]string{host}, pubKey)
+	if _, err = f.WriteString("\n" + l + "\n"); err != nil {
+		return err
+	}
+	logrus.Infof("key %s added to %s", ssh.FingerprintSHA256(pubKey), known)
+	return nil
+}
diff --git a/pkg/ssh/types.go b/pkg/ssh/types.go
index f22b5fba9..16512c43f 100644
--- a/pkg/ssh/types.go
+++ b/pkg/ssh/types.go
@@ -27,12 +27,13 @@ type ConnectionCreateOptions struct {
 }
 
 type ConnectionDialOptions struct {
-	Host     string
-	Identity string
-	User     *url.Userinfo
-	Port     int
-	Auth     []string
-	Timeout  time.Duration
+	Host                        string
+	Identity                    string
+	User                        *url.Userinfo
+	Port                        int
+	Auth                        []string
+	Timeout                     time.Duration
+	InsecureIsMachineConnection bool
 }
 
 type ConnectionDialReport struct {
diff --git a/pkg/ssh/utils.go b/pkg/ssh/utils.go
index c15745015..b05105d9c 100644
--- a/pkg/ssh/utils.go
+++ b/pkg/ssh/utils.go
@@ -21,6 +21,7 @@ func Validate(user *url.Userinfo, path string, port int, identity string) (*conf
 	if strings.Contains(path, "/run") {
 		sock = strings.Split(path, "/run")[1]
 	}
+	// url.Parse NEEDS ssh://, if this ever fails or returns some nonsense, that is why.
 	uri, err := url.Parse(path)
 	if err != nil {
 		return nil, nil, err
@@ -33,9 +34,9 @@ func Validate(user *url.Userinfo, path string, port int, identity string) (*conf
 
 	if uri.Port() == "" {
 		if port != 0 {
-			uri.Host = net.JoinHostPort(uri.Hostname(), strconv.Itoa(port))
+			uri.Host = net.JoinHostPort(uri.Host, strconv.Itoa(port))
 		} else {
-			uri.Host = net.JoinHostPort(uri.Hostname(), "22")
+			uri.Host = net.JoinHostPort(uri.Host, "22")
 		}
 	}