diff --git a/libpod/networking_machine.go b/libpod/networking_machine.go
index de45e299ea..1212b03ed1 100644
--- a/libpod/networking_machine.go
+++ b/libpod/networking_machine.go
@@ -75,7 +75,7 @@ func requestMachinePorts(expose bool, ports []types.PortMapping) error {
 					}
 					return err
 				}
-				if err := makeMachineRequest(ctx, client, url, buf); err != nil {
+				if err := makeMachineRequest(ctx, client, url, buf, machinePort); err != nil {
 					if expose {
 						// in case of an error make sure to unexpose the other ports
 						if cerr := requestMachinePorts(false, ports[:num]); cerr != nil {
@@ -91,7 +91,7 @@ func requestMachinePorts(expose bool, ports []types.PortMapping) error {
 	return nil
 }
 
-func makeMachineRequest(ctx context.Context, client *http.Client, url string, buf io.Reader) error {
+func makeMachineRequest(ctx context.Context, client *http.Client, url string, buf io.Reader, port machineExpose) error {
 	req, err := http.NewRequestWithContext(ctx, http.MethodPost, url, buf)
 	if err != nil {
 		return err
@@ -104,19 +104,41 @@ func makeMachineRequest(ctx context.Context, client *http.Client, url string, bu
 	}
 	defer resp.Body.Close()
 	if resp.StatusCode != http.StatusOK {
-		return annotateGvproxyResponseError(resp.Body)
+		return annotateGvproxyResponseError(resp.Body, port)
 	}
 	return nil
 }
 
-func annotateGvproxyResponseError(r io.Reader) error {
+func annotateGvproxyResponseError(r io.Reader, port machineExpose) error {
 	b, err := io.ReadAll(r)
 	if err == nil && len(b) > 0 {
-		return fmt.Errorf("something went wrong with the request: %q", string(b))
+		body := string(b)
+		// gvproxy runs unprivileged on the host and binds the published port
+		// there, not inside the VM. On macOS, binding a privileged port
+		// (< 1024) to a specific IP address is rejected for a normal user even
+		// though binding to all interfaces is allowed, so give a more
+		// actionable error in that case instead of the raw gvproxy message.
+		// See https://github.com/containers/podman/issues/28009
+		if host, portStr, perr := net.SplitHostPort(port.Local); perr == nil && strings.Contains(body, "permission denied") {
+			if p, cerr := strconv.Atoi(portStr); cerr == nil && p < 1024 && !unspecifiedHostIP(host) {
+				return fmt.Errorf("cannot bind port %s: %q: with podman machine the published port is bound on the host by gvproxy, which runs unprivileged; macOS does not permit binding a privileged port (< 1024) to a specific IP address as a normal user. Publish the port without a host IP to bind all interfaces, or use a port >= 1024", port.Local, body)
+			}
+		}
+		return fmt.Errorf("something went wrong with the request: %q", body)
 	}
 	return errors.New("something went wrong with the request, could not read response")
 }
 
+// unspecifiedHostIP reports whether the host part of a published port maps to
+// "all interfaces": an empty host or the unspecified address (0.0.0.0 / ::).
+func unspecifiedHostIP(host string) bool {
+	if host == "" {
+		return true
+	}
+	ip := net.ParseIP(host)
+	return ip != nil && ip.IsUnspecified()
+}
+
 // exposeMachinePorts exposes the ports for podman machine via gvproxy
 func (r *Runtime) exposeMachinePorts(ports []types.PortMapping) error {
 	if !machine.IsGvProxyBased() {
diff --git a/libpod/networking_machine_test.go b/libpod/networking_machine_test.go
new file mode 100644
index 0000000000..24aad2027b
--- /dev/null
+++ b/libpod/networking_machine_test.go
@@ -0,0 +1,52 @@
+//go:build !remote && (linux || freebsd)
+
+package libpod
+
+import (
+	"strings"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestAnnotateGvproxyResponseError(t *testing.T) {
+	const permDenied = "bind: permission denied"
+
+	tests := []struct {
+		name string
+		body string
+		// local is the host-side "ip:port" gvproxy was asked to bind.
+		local string
+		// wantHint is true when the macOS/gvproxy privileged-port hint is expected.
+		wantHint bool
+	}{
+		{"privileged port on a specific IP returns the gvproxy hint", permDenied, "192.168.1.5:80", true},
+		{"privileged port on an IPv6 address returns the gvproxy hint", permDenied, "[fe80::1]:443", true},
+		{"privileged port without a host IP stays generic", permDenied, ":80", false},
+		{"privileged port on 0.0.0.0 stays generic", permDenied, "0.0.0.0:80", false},
+		{"privileged port on the IPv6 unspecified address stays generic", permDenied, "[::]:80", false},
+		{"unprivileged port on a specific IP stays generic", permDenied, "192.168.1.5:8080", false},
+		{"unrelated error on a specific privileged port stays generic", "some other failure", "192.168.1.5:80", false},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			err := annotateGvproxyResponseError(strings.NewReader(tt.body), machineExpose{Local: tt.local})
+			require.Error(t, err)
+			assert.Equal(t, tt.wantHint, strings.Contains(err.Error(), "gvproxy"))
+			if tt.wantHint {
+				// the hint must carry the actionable guidance, not just the word "gvproxy"
+				assert.Contains(t, err.Error(), "without a host IP")
+			}
+			// The raw gvproxy response body is always preserved for debugging.
+			assert.Contains(t, err.Error(), tt.body)
+		})
+	}
+}
+
+func TestAnnotateGvproxyResponseErrorEmptyBody(t *testing.T) {
+	err := annotateGvproxyResponseError(strings.NewReader(""), machineExpose{Local: "192.168.1.5:80"})
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "could not read response")
+}