diff --git a/pkg/machine/apple/apple.go b/pkg/machine/apple/apple.go
index f4aab463bf..93201407e9 100644
--- a/pkg/machine/apple/apple.go
+++ b/pkg/machine/apple/apple.go
@@ -96,19 +96,19 @@ func GenerateSystemDFilesForVirtiofsMounts(mounts []machine.VirtIoFs) ([]ignitio
 
 		virtiofsAutomount := ignition.Unit{
 			Enabled:  ignition.BoolToPtr(true),
-			Name:     fmt.Sprintf("%s.automount", mnt.Tag),
-			Contents: ignition.StrToPtr(fmt.Sprintf(autoMountUnitFile, mnt.Target, mnt.Target)),
+			Name:     fmt.Sprintf("%s.automount", parser.PathEscape(mnt.Target)),
+			Contents: ignition.StrToPtr(fmt.Sprintf(autoMountUnitFile, mnt.Tag, mnt.Target)),
 		}
 		virtiofsMount := ignition.Unit{
 			Enabled:  ignition.BoolToPtr(true),
-			Name:     fmt.Sprintf("%s.mount", mnt.Tag),
+			Name:     fmt.Sprintf("%s.mount", parser.PathEscape(mnt.Target)),
 			Contents: ignition.StrToPtr(fmt.Sprintf(mountUnitFile, mnt.Tag, mnt.Target)),
 		}
 
 		// This "unit" simulates something like systemctl enable virtiofs-mount-prepare@
 		enablePrep := ignition.Unit{
 			Enabled: ignition.BoolToPtr(true),
-			Name:    fmt.Sprintf("virtiofs-mount-prepare@%s.service", mnt.Tag),
+			Name:    fmt.Sprintf("virtiofs-mount-prepare@%s.service", parser.PathEscape(mnt.Target)),
 		}
 
 		unitFiles = append(unitFiles, virtiofsAutomount, virtiofsMount, enablePrep)
diff --git a/pkg/machine/e2e/init_test.go b/pkg/machine/e2e/init_test.go
index daf4880ef6..e3844cb8c2 100644
--- a/pkg/machine/e2e/init_test.go
+++ b/pkg/machine/e2e/init_test.go
@@ -207,7 +207,8 @@ var _ = Describe("podman machine init", func() {
 		Expect(err).ToNot(HaveOccurred())
 		_, err = os.CreateTemp(tmpDir, "example")
 		Expect(err).ToNot(HaveOccurred())
-		mount := tmpDir + ":/testmountdir"
+		// Test long target path, see https://github.com/containers/podman/issues/22226
+		mount := tmpDir + ":/very-long-test-mount-dir-path-more-than-thirty-six-bytes"
 		defer func() { _ = utils.GuardedRemoveAll(tmpDir) }()
 
 		name := randomString()
@@ -217,7 +218,7 @@ var _ = Describe("podman machine init", func() {
 		Expect(session).To(Exit(0))
 
 		ssh := sshMachine{}
-		sshSession, err := mb.setName(name).setCmd(ssh.withSSHCommand([]string{"ls /testmountdir"})).run()
+		sshSession, err := mb.setName(name).setCmd(ssh.withSSHCommand([]string{"ls /very-long-test-mount-dir-path-more-than-thirty-six-bytes"})).run()
 		Expect(err).ToNot(HaveOccurred())
 		Expect(sshSession).To(Exit(0))
 		Expect(sshSession.outputToString()).To(ContainSubstring("example"))
diff --git a/pkg/machine/volumes.go b/pkg/machine/volumes.go
index b451e8c634..8fda9155e3 100644
--- a/pkg/machine/volumes.go
+++ b/pkg/machine/volumes.go
@@ -1,7 +1,8 @@
 package machine
 
 import (
-	"strings"
+	"crypto/sha256"
+	"encoding/hex"
 
 	"github.com/containers/podman/v5/pkg/machine/vmconfigs"
 )
@@ -29,14 +30,13 @@ func (v VirtIoFs) Kind() string {
 	return string(VirtIOFsVk)
 }
 
-// unitName is the fq path where /'s are replaced with -'s
-func (v VirtIoFs) unitName() string {
-	// delete the leading -
-	unit := strings.ReplaceAll(v.Target, "/", "-")
-	if strings.HasPrefix(unit, "-") {
-		return unit[1:]
-	}
-	return unit
+// generateTag generates a tag for VirtIOFs mounts.
+// AppleHV requires tags to be 36 bytes or fewer.
+// SHA256 the path, then truncate to 36 bytes
+func (v VirtIoFs) generateTag() string {
+	sum := sha256.Sum256([]byte(v.Target))
+	stringSum := hex.EncodeToString(sum[:])
+	return stringSum[:36]
 }
 
 func (v VirtIoFs) ToMount() vmconfigs.Mount {
@@ -58,7 +58,7 @@ func NewVirtIoFsMount(src, target string, readOnly bool) VirtIoFs {
 		Source:   src,
 		Target:   target,
 	}
-	vfs.Tag = vfs.unitName()
+	vfs.Tag = vfs.generateTag()
 	return vfs
 }
 
diff --git a/pkg/systemd/parser/split.go b/pkg/systemd/parser/split.go
index c2778032a9..433e869a65 100644
--- a/pkg/systemd/parser/split.go
+++ b/pkg/systemd/parser/split.go
@@ -428,13 +428,17 @@ func splitString(s string, separators string, flags SplitFlags) ([]string, error
 	return splitStringAppend(make([]string, 0), s, separators, flags)
 }
 
-func charNeedEscape(c rune) bool {
+func charNeedEscape(c rune, isPath bool) bool {
 	if c > 128 {
 		return false /* unicode is ok */
 	}
 
+	pathRune := (isPath && c == '-') ||
+		(isPath && c == '/')
+
 	return unicode.IsSpace(c) ||
 		unicode.IsControl(c) ||
+		pathRune ||
 		c == '"' ||
 		c == '\'' ||
 		c == '\\'
@@ -442,18 +446,22 @@ func charNeedEscape(c rune) bool {
 
 func wordNeedEscape(word string) bool {
 	for _, c := range word {
-		if charNeedEscape(c) {
+		if charNeedEscape(c, false) {
 			return true
 		}
 	}
-
 	return false
 }
 
 func appendEscapeWord(escaped *strings.Builder, word string) {
 	escaped.WriteRune('"')
-	for _, c := range word {
-		if charNeedEscape(c) {
+	escapeString(escaped, word, false)
+	escaped.WriteRune('"')
+}
+
+func escapeString(escaped *strings.Builder, word string, isPath bool) {
+	for i, c := range word {
+		if charNeedEscape(c, isPath) {
 			switch c {
 			case '\a':
 				escaped.WriteString("\\a")
@@ -477,6 +485,10 @@ func appendEscapeWord(escaped *strings.Builder, word string) {
 				escaped.WriteString("\\\"")
 			case '\'':
 				escaped.WriteString("'")
+			case '/':
+				if isPath && i != 0 {
+					escaped.WriteString("-")
+				}
 			default:
 				escaped.WriteString(fmt.Sprintf("\\x%.2x", c))
 			}
@@ -484,7 +496,6 @@ func appendEscapeWord(escaped *strings.Builder, word string) {
 			escaped.WriteRune(c)
 		}
 	}
-	escaped.WriteRune('"')
 }
 
 func escapeWords(words []string) string {
@@ -500,6 +511,5 @@ func escapeWords(words []string) string {
 			escaped.WriteString(word)
 		}
 	}
-
 	return escaped.String()
 }
diff --git a/pkg/systemd/parser/unitfile.go b/pkg/systemd/parser/unitfile.go
index b7b47d54a1..e9b0186611 100644
--- a/pkg/systemd/parser/unitfile.go
+++ b/pkg/systemd/parser/unitfile.go
@@ -932,3 +932,9 @@ func (f *UnitFile) GetTemplateParts() (string, string) {
 	}
 	return parts[0] + "@" + ext, parts[1]
 }
+
+func PathEscape(path string) string {
+	var escaped strings.Builder
+	escapeString(&escaped, path, true)
+	return escaped.String()
+}