diff --git a/pkg/machine/connection/connection.go b/pkg/machine/connection/connection.go
index 2dea2d93f9..469dadcb1e 100644
--- a/pkg/machine/connection/connection.go
+++ b/pkg/machine/connection/connection.go
@@ -64,7 +64,7 @@ func UpdateConnectionPairPort(name string, port, uid int, remoteUsername string,
 				URI:       con.uri.String(),
 				Identity:  identityPath,
 			}
-			cfg.Connection.Connections[name] = dst
+			cfg.Connection.Connections[con.name] = dst
 		}
 
 		return nil
diff --git a/pkg/machine/e2e/config_system_connection_list_test.go b/pkg/machine/e2e/config_system_connection_list_test.go
new file mode 100644
index 0000000000..cc52745e2d
--- /dev/null
+++ b/pkg/machine/e2e/config_system_connection_list_test.go
@@ -0,0 +1,23 @@
+package e2e_test
+
+type listSystemConnection struct {
+	/*
+		--format string   Custom Go template for printing connections
+	*/
+
+	format string
+}
+
+func (l listSystemConnection) buildCmd(m *machineTestBuilder) []string {
+	cmd := []string{"system", "connection", "list"}
+	if len(l.format) > 0 {
+		cmd = append(cmd, "--format", l.format)
+	}
+
+	return cmd
+}
+
+func (l *listSystemConnection) withFormat(format string) *listSystemConnection {
+	l.format = format
+	return l
+}
diff --git a/pkg/machine/e2e/start_test.go b/pkg/machine/e2e/start_test.go
index 3803986d2d..5b2a6342ef 100644
--- a/pkg/machine/e2e/start_test.go
+++ b/pkg/machine/e2e/start_test.go
@@ -1,6 +1,9 @@
 package e2e_test
 
 import (
+	"fmt"
+	"net"
+	"net/url"
 	"sync"
 	"time"
 
@@ -88,6 +91,55 @@ var _ = Describe("podman machine start", func() {
 		Expect(startSession.errorToString()).To(ContainSubstring("VM already running or starting"))
 	})
 
+	It("start machine with conflict on SSH port", func() {
+		i := new(initMachine)
+		session, err := mb.setCmd(i.withImage(mb.imagePath)).run()
+		Expect(err).ToNot(HaveOccurred())
+		Expect(session).To(Exit(0))
+
+		inspect := new(inspectMachine)
+		inspectSession, err := mb.setCmd(inspect.withFormat("{{.SSHConfig.Port}}")).run()
+		Expect(err).ToNot(HaveOccurred())
+		Expect(inspectSession).To(Exit(0))
+		inspectPort := inspectSession.outputToString()
+
+		connections := new(listSystemConnection)
+		connectionsSession, err := mb.setCmd(connections.withFormat("{{.URI}}")).run()
+		Expect(err).ToNot(HaveOccurred())
+		Expect(connectionsSession).To(Exit(0))
+		connectionURLs := connectionsSession.outputToStringSlice()
+		connectionPorts, err := mapToPort(connectionURLs)
+		Expect(err).ToNot(HaveOccurred())
+		Expect(connectionPorts).To(HaveEach(inspectPort))
+
+		// start a listener on the ssh port
+		listener, err := net.Listen("tcp", "127.0.0.1:"+inspectPort)
+		Expect(err).ToNot(HaveOccurred())
+		defer listener.Close()
+
+		s := new(startMachine)
+		startSession, err := mb.setCmd(s).run()
+		Expect(err).ToNot(HaveOccurred())
+		Expect(startSession).To(Exit(0))
+		Expect(startSession.errorToString()).To(ContainSubstring("detected port conflict on machine ssh port"))
+
+		inspect2 := new(inspectMachine)
+		inspectSession2, err := mb.setCmd(inspect2.withFormat("{{.SSHConfig.Port}}")).run()
+		Expect(err).ToNot(HaveOccurred())
+		Expect(inspectSession2).To(Exit(0))
+		inspectPort2 := inspectSession2.outputToString()
+		Expect(inspectPort2).To(Not(Equal(inspectPort)))
+
+		connections2 := new(listSystemConnection)
+		connectionsSession2, err := mb.setCmd(connections2.withFormat("{{.URI}}")).run()
+		Expect(err).ToNot(HaveOccurred())
+		Expect(connectionsSession2).To(Exit(0))
+		connectionURLs2 := connectionsSession2.outputToStringSlice()
+		connectionPorts2, err := mapToPort(connectionURLs2)
+		Expect(err).ToNot(HaveOccurred())
+		Expect(connectionPorts2).To(HaveEach(inspectPort2))
+	})
+
 	It("start only starts specified machine", func() {
 		i := initMachine{}
 		startme := randomString()
@@ -175,3 +227,22 @@ var _ = Describe("podman machine start", func() {
 		}
 	})
 })
+
+func mapToPort(uris []string) ([]string, error) {
+	ports := []string{}
+
+	for _, uri := range uris {
+		u, err := url.Parse(uri)
+		if err != nil {
+			return nil, err
+		}
+
+		port := u.Port()
+		if port == "" {
+			return nil, fmt.Errorf("no port in URI: %s", uri)
+		}
+
+		ports = append(ports, port)
+	}
+	return ports, nil
+}