diff --git a/cmd/podman/images/pull.go b/cmd/podman/images/pull.go
index 4604565e2d..2bcfd2055c 100644
--- a/cmd/podman/images/pull.go
+++ b/cmd/podman/images/pull.go
@@ -110,7 +110,7 @@ func pullFlags(cmd *cobra.Command) {
 	_ = cmd.RegisterFlagCompletionFunc(authfileFlagName, completion.AutocompleteDefault)
 
 	decryptionKeysFlagName := "decryption-key"
-	flags.StringSliceVar(&pullOptions.DecryptionKeys, decryptionKeysFlagName, nil, "Key needed to decrypt the image (e.g. /path/to/key.pem)")
+	flags.StringArrayVar(&pullOptions.DecryptionKeys, decryptionKeysFlagName, nil, "Key needed to decrypt the image (e.g. /path/to/key.pem)")
 	_ = cmd.RegisterFlagCompletionFunc(decryptionKeysFlagName, completion.AutocompleteDefault)
 
 	if registry.IsRemote() {
diff --git a/cmd/podman/images/push.go b/cmd/podman/images/push.go
index 6d22a61032..168411328f 100644
--- a/cmd/podman/images/push.go
+++ b/cmd/podman/images/push.go
@@ -138,7 +138,7 @@ func pushFlags(cmd *cobra.Command) {
 	_ = cmd.RegisterFlagCompletionFunc(compLevel, completion.AutocompleteNone)
 
 	encryptionKeysFlagName := "encryption-key"
-	flags.StringSliceVar(&pushOptions.EncryptionKeys, encryptionKeysFlagName, nil, "Key with the encryption protocol to use to encrypt the image (e.g. jwe:/path/to/key.pem)")
+	flags.StringArrayVar(&pushOptions.EncryptionKeys, encryptionKeysFlagName, nil, "Key with the encryption protocol to use to encrypt the image (e.g. jwe:/path/to/key.pem)")
 	_ = cmd.RegisterFlagCompletionFunc(encryptionKeysFlagName, completion.AutocompleteDefault)
 
 	encryptLayersFlagName := "encrypt-layer"
diff --git a/cmd/podman/images/trust_set.go b/cmd/podman/images/trust_set.go
index e7339f0b18..2ed91d9c46 100644
--- a/cmd/podman/images/trust_set.go
+++ b/cmd/podman/images/trust_set.go
@@ -41,7 +41,7 @@ func init() {
 	_ = setFlags.MarkHidden("policypath")
 
 	pubkeysfileFlagName := "pubkeysfile"
-	setFlags.StringSliceVarP(&setOptions.PubKeysFile, pubkeysfileFlagName, "f", []string{}, `Path of installed public key(s) to trust for TARGET.
+	setFlags.StringArrayVarP(&setOptions.PubKeysFile, pubkeysfileFlagName, "f", []string{}, `Path of installed public key(s) to trust for TARGET.
 Absolute path to keys is added to policy.json. May
 used multiple times to define multiple public keys.
 File(s) must exist before using this command`)
diff --git a/cmd/podman/kube/play.go b/cmd/podman/kube/play.go
index 8ca7354dc6..f2d2565c88 100644
--- a/cmd/podman/kube/play.go
+++ b/cmd/podman/kube/play.go
@@ -98,7 +98,7 @@ func playFlags(cmd *cobra.Command) {
 	flags.SetNormalizeFunc(utils.AliasFlags)
 
 	annotationFlagName := "annotation"
-	flags.StringSliceVar(
+	flags.StringArrayVar(
 		&playOptions.annotations,
 		annotationFlagName, []string{},
 		"Add annotations to pods (key=value)",
@@ -124,7 +124,7 @@ func playFlags(cmd *cobra.Command) {
 	_ = cmd.RegisterFlagCompletionFunc(logDriverFlagName, common.AutocompleteLogDriver)
 
 	logOptFlagName := "log-opt"
-	flags.StringSliceVar(
+	flags.StringArrayVar(
 		&playOptions.LogOptions,
 		logOptFlagName, []string{},
 		"Logging driver options",
@@ -165,7 +165,7 @@ func playFlags(cmd *cobra.Command) {
 	flags.BoolVarP(&playOptions.Wait, waitFlagName, "w", false, "Clean up all objects created when a SIGTERM is received or pods exit")
 
 	configmapFlagName := "configmap"
-	flags.StringSliceVar(&playOptions.ConfigMaps, configmapFlagName, []string{}, "`Pathname` of a YAML file containing a kubernetes configmap")
+	flags.StringArrayVar(&playOptions.ConfigMaps, configmapFlagName, []string{}, "`Pathname` of a YAML file containing a kubernetes configmap")
 	_ = cmd.RegisterFlagCompletionFunc(configmapFlagName, completion.AutocompleteDefault)
 
 	noTruncFlagName := "no-trunc"
@@ -239,7 +239,7 @@ func play(cmd *cobra.Command, args []string) error {
 
 	for _, annotation := range playOptions.annotations {
 		splitN := strings.SplitN(annotation, "=", 2)
-		if len(splitN) > 2 {
+		if len(splitN) != 2 {
 			return fmt.Errorf("annotation %q must include an '=' sign", annotation)
 		}
 		if playOptions.Annotations == nil {
diff --git a/cmd/podman/manifest/add.go b/cmd/podman/manifest/add.go
index 490be688b9..f957ee4632 100644
--- a/cmd/podman/manifest/add.go
+++ b/cmd/podman/manifest/add.go
@@ -48,7 +48,7 @@ func init() {
 	flags.BoolVar(&manifestAddOpts.All, "all", false, "add all of the list's images if the image is a list")
 
 	annotationFlagName := "annotation"
-	flags.StringSliceVar(&manifestAddOpts.Annotation, annotationFlagName, nil, "set an `annotation` for the specified image")
+	flags.StringArrayVar(&manifestAddOpts.Annotation, annotationFlagName, nil, "set an `annotation` for the specified image")
 	_ = addCmd.RegisterFlagCompletionFunc(annotationFlagName, completion.AutocompleteNone)
 
 	archFlagName := "arch"
diff --git a/cmd/podman/manifest/annotate.go b/cmd/podman/manifest/annotate.go
index 73f1b18cbd..c628e3e0fe 100644
--- a/cmd/podman/manifest/annotate.go
+++ b/cmd/podman/manifest/annotate.go
@@ -31,7 +31,7 @@ func init() {
 	flags := annotateCmd.Flags()
 
 	annotationFlagName := "annotation"
-	flags.StringSliceVar(&manifestAnnotateOpts.Annotation, annotationFlagName, nil, "set an `annotation` for the specified image")
+	flags.StringArrayVar(&manifestAnnotateOpts.Annotation, annotationFlagName, nil, "set an `annotation` for the specified image")
 	_ = annotateCmd.RegisterFlagCompletionFunc(annotationFlagName, completion.AutocompleteNone)
 
 	archFlagName := "arch"
diff --git a/test/e2e/manifest_test.go b/test/e2e/manifest_test.go
index 744108dcff..071239f4fb 100644
--- a/test/e2e/manifest_test.go
+++ b/test/e2e/manifest_test.go
@@ -314,7 +314,7 @@ add_compression = ["zstd"]`), 0o644)
 		session.WaitWithDefaultTimeout()
 		Expect(session).Should(Exit(125))
 		Expect(session.ErrorToString()).To(ContainSubstring("no value given for annotation"))
-		session = podmanTest.Podman([]string{"manifest", "add", "--annotation", "hoge=fuga", "foo", imageList})
+		session = podmanTest.Podman([]string{"manifest", "add", "--annotation", "hoge=fuga", "--annotation", "key=val,withcomma", "foo", imageList})
 		session.WaitWithDefaultTimeout()
 		Expect(session).Should(ExitCleanly())
 		session = podmanTest.Podman([]string{"manifest", "inspect", "foo"})
@@ -324,7 +324,7 @@ add_compression = ["zstd"]`), 0o644)
 		var inspect define.ManifestListData
 		err := json.Unmarshal(session.Out.Contents(), &inspect)
 		Expect(err).ToNot(HaveOccurred())
-		Expect(inspect.Manifests[0].Annotations).To(Equal(map[string]string{"hoge": "fuga"}))
+		Expect(inspect.Manifests[0].Annotations).To(Equal(map[string]string{"hoge": "fuga", "key": "val,withcomma"}))
 	})
 
 	It("add --os", func() {
@@ -347,7 +347,7 @@ add_compression = ["zstd"]`), 0o644)
 		session = podmanTest.Podman([]string{"manifest", "add", "foo", imageListInstance})
 		session.WaitWithDefaultTimeout()
 		Expect(session).Should(ExitCleanly())
-		session = podmanTest.Podman([]string{"manifest", "annotate", "--annotation", "hello=world", "--arch", "bar", "foo", imageListARM64InstanceDigest})
+		session = podmanTest.Podman([]string{"manifest", "annotate", "--annotation", "hello=world,withcomma", "--arch", "bar", "foo", imageListARM64InstanceDigest})
 		session.WaitWithDefaultTimeout()
 		Expect(session).Should(ExitCleanly())
 		session = podmanTest.Podman([]string{"manifest", "inspect", "foo"})
@@ -355,7 +355,7 @@ add_compression = ["zstd"]`), 0o644)
 		Expect(session).Should(ExitCleanly())
 		Expect(session.OutputToString()).To(ContainSubstring(`"architecture": "bar"`))
 		// Check added annotation
-		Expect(session.OutputToString()).To(ContainSubstring(`"hello": "world"`))
+		Expect(session.OutputToString()).To(ContainSubstring(`"hello": "world,withcomma"`))
 	})
 
 	It("remove digest", func() {
diff --git a/test/e2e/play_kube_test.go b/test/e2e/play_kube_test.go
index 77aed75e86..8581af4384 100644
--- a/test/e2e/play_kube_test.go
+++ b/test/e2e/play_kube_test.go
@@ -4886,7 +4886,7 @@ ENV OPENJ9_JAVA_OPTIONS=%q
 		err := generateKubeYaml("pod", pod, kubeYaml)
 		Expect(err).ToNot(HaveOccurred())
 
-		kube := podmanTest.Podman([]string{"kube", "play", kubeYaml, "--log-driver", "journald", "--log-opt", "tag={{.ImageName}}"})
+		kube := podmanTest.Podman([]string{"kube", "play", kubeYaml, "--log-driver", "journald", "--log-opt", "tag={{.ImageName}},withcomma"})
 		kube.WaitWithDefaultTimeout()
 		Expect(kube).Should(ExitCleanly())
 
@@ -4897,7 +4897,7 @@ ENV OPENJ9_JAVA_OPTIONS=%q
 		inspect := podmanTest.Podman([]string{"inspect", getCtrNameInPod(pod)})
 		inspect.WaitWithDefaultTimeout()
 		Expect(start).Should(ExitCleanly())
-		Expect((inspect.InspectContainerToJSON()[0]).HostConfig.LogConfig.Tag).To(Equal("{{.ImageName}}"))
+		Expect((inspect.InspectContainerToJSON()[0]).HostConfig.LogConfig.Tag).To(Equal("{{.ImageName}},withcomma"))
 	})
 
 	It("using a user namespace", func() {
diff --git a/test/e2e/pull_test.go b/test/e2e/pull_test.go
index 9a3b5f049f..465786917f 100644
--- a/test/e2e/pull_test.go
+++ b/test/e2e/pull_test.go
@@ -612,7 +612,7 @@ var _ = Describe("Podman pull", func() {
 
 		decryptionTestHelper := func(imgPath string) *PodmanSessionIntegration {
 			bitSize := 1024
-			keyFileName := filepath.Join(podmanTest.TempDir, "key")
+			keyFileName := filepath.Join(podmanTest.TempDir, "key,withcomma")
 			publicKeyFileName, privateKeyFileName, err := WriteRSAKeyPair(keyFileName, bitSize)
 			Expect(err).ToNot(HaveOccurred())
 
diff --git a/test/e2e/run_test.go b/test/e2e/run_test.go
index f07ece51cf..b42b2b661c 100644
--- a/test/e2e/run_test.go
+++ b/test/e2e/run_test.go
@@ -2152,7 +2152,7 @@ WORKDIR /madethis`, BB)
 		}
 
 		bitSize := 1024
-		keyFileName := filepath.Join(podmanTest.TempDir, "key")
+		keyFileName := filepath.Join(podmanTest.TempDir, "key,withcomma")
 		publicKeyFileName, privateKeyFileName, err := WriteRSAKeyPair(keyFileName, bitSize)
 		Expect(err).ToNot(HaveOccurred())
 
diff --git a/test/system/700-play.bats b/test/system/700-play.bats
index bb8d85ff4b..f5c8631ad5 100644
--- a/test/system/700-play.bats
+++ b/test/system/700-play.bats
@@ -435,11 +435,18 @@ _EOF
 @test "podman kube --annotation" {
     TESTDIR=$PODMAN_TMPDIR/testdir
     RANDOMSTRING=$(random_string 15)
+    ANNOTATION_WITH_COMMA="comma,$(random_string 5)"
     mkdir -p $TESTDIR
     echo "$testYaml" | sed "s|TESTDIR|${TESTDIR}|g" > $PODMAN_TMPDIR/test.yaml
-    run_podman kube play --annotation "name=$RANDOMSTRING" $PODMAN_TMPDIR/test.yaml
+    run_podman kube play --annotation "name=$RANDOMSTRING"  \
+        --annotation "anno=$ANNOTATION_WITH_COMMA" $PODMAN_TMPDIR/test.yaml
     run_podman inspect --format "{{ .Config.Annotations }}" test_pod-test
     is "$output" ".*name:$RANDOMSTRING" "Annotation should be added to pod"
+    is "$output" ".*anno:$ANNOTATION_WITH_COMMA" "Annotation with comma should be added to pod"
+
+    # invalid annotation
+    run_podman 125 kube play --annotation "val" $PODMAN_TMPDIR/test.yaml
+    assert "$output" == "Error: annotation \"val\" must include an '=' sign" "invalid annotation error"
 
     run_podman stop -a -t 0
     run_podman pod rm -t 0 -f test_pod
@@ -692,7 +699,7 @@ spec:
 }
 
 @test "podman kube play with configmaps" {
-    configmap_file=${PODMAN_TMPDIR}/play_kube_configmap_configmaps$(random_string 6).yaml
+    configmap_file=${PODMAN_TMPDIR}/play_kube_configmap_configmaps$(random_string 6),withcomma.yaml
     echo "
 ---
 apiVersion: v1