diff --git a/docs/content/en/schemas/v1beta11.json b/docs/content/en/schemas/v1beta11.json
index 09aaaedb462..8ea958aec95 100755
--- a/docs/content/en/schemas/v1beta11.json
+++ b/docs/content/en/schemas/v1beta11.json
@@ -1674,8 +1674,8 @@
         },
         "src": {
           "type": "string",
-          "description": "a glob pattern to match local paths against.",
-          "x-intellij-html-description": "a glob pattern to match local paths against.",
+          "description": "a glob pattern to match local paths against. Directories should be delimited by `/` on all platforms.",
+          "x-intellij-html-description": "a glob pattern to match local paths against. Directories should be delimited by <code>/</code> on all platforms.",
           "examples": [
             "\"css/**/*.css\""
           ]
diff --git a/pkg/skaffold/schema/latest/config.go b/pkg/skaffold/schema/latest/config.go
index 65930e23c78..cf085e53949 100644
--- a/pkg/skaffold/schema/latest/config.go
+++ b/pkg/skaffold/schema/latest/config.go
@@ -498,6 +498,7 @@ type Sync struct {
 // SyncRule specifies which local files to sync to remote folders.
 type SyncRule struct {
 	// Src is a glob pattern to match local paths against.
+	// Directories should be delimited by `/` on all platforms.
 	// For example: `"css/**/*.css"`.
 	Src string `yaml:"src,omitempty" yamltags:"required"`
 
diff --git a/pkg/skaffold/schema/v1beta9/upgrade.go b/pkg/skaffold/schema/v1beta9/upgrade.go
index b9d0653359c..02f318f76d0 100644
--- a/pkg/skaffold/schema/v1beta9/upgrade.go
+++ b/pkg/skaffold/schema/v1beta9/upgrade.go
@@ -17,6 +17,7 @@ limitations under the License.
 package v1beta9
 
 import (
+	"regexp"
 	"strings"
 
 	"github.com/GoogleContainerTools/skaffold/pkg/skaffold/schema/util"
@@ -30,6 +31,11 @@ const (
 	incompatibleSyncWarning = `The semantics of sync has changed, the folder structure is no longer flattened but preserved (see https://skaffold.dev/docs/how-tos/filesync/). The likely impacted patterns in your skaffold yaml are: %s`
 )
 
+var (
+	// compatibleSimplePattern have a directory prefix without stars and a basename with at most one star.
+	compatibleSimplePattern = regexp.MustCompile(`^([^*]*/)?([^*/]*\*[^*/]*|[^*/]+)$`)
+)
+
 // Upgrade upgrades a configuration to the next version.
 // Config changes from v1beta9 to v1beta10
 // 1. Additions:
@@ -94,17 +100,25 @@ func (config *SkaffoldConfig) convertSyncRules() [][]*next.SyncRule {
 		newRules := make([]*next.SyncRule, 0, len(a.Sync))
 		for src, dest := range a.Sync {
 			var syncRule *next.SyncRule
-			if strings.Contains(src, "***") {
+			switch {
+			case compatibleSimplePattern.MatchString(src):
+				syncRule = &next.SyncRule{
+					Src:   src,
+					Dest:  dest,
+					Strip: compatibleSimplePattern.FindStringSubmatch(src)[1],
+				}
+			case strings.Contains(src, "***"):
 				syncRule = &next.SyncRule{
 					Src:   strings.Replace(src, "***", "**", -1),
 					Dest:  dest,
 					Strip: strings.Split(src, "***")[0],
 				}
-			} else {
-				// only patterns with '**' are incompatible
-				if strings.Contains(src, "**") {
-					incompatiblePatterns = append(incompatiblePatterns, src)
-				}
+			default:
+				// Incompatible patterns contain `**` or glob directories.
+				// Such patterns flatten the content at the destination which
+				// cannot be reproduced with the current config. For example:
+				// `/app/**/subdir/*.html`, `/app/*/*.html`
+				incompatiblePatterns = append(incompatiblePatterns, src)
 				syncRule = &next.SyncRule{
 					Src:  src,
 					Dest: dest,
diff --git a/pkg/skaffold/schema/v1beta9/upgrade_test.go b/pkg/skaffold/schema/v1beta9/upgrade_test.go
index f2449f203e3..7b356fa4ece 100644
--- a/pkg/skaffold/schema/v1beta9/upgrade_test.go
+++ b/pkg/skaffold/schema/v1beta9/upgrade_test.go
@@ -140,10 +140,33 @@ apiVersion: skaffold/v1beta9
 kind: Config
 build:
   artifacts:
+  - image: gcr.io/no-star-1
+    sync:
+      '/public/A/B/a.html': /www
+  - image: gcr.io/no-star-2
+    sync:
+      '/b.html': /www
+  - image: gcr.io/no-star-3
+    sync:
+      'c.html': /www
+  - image: gcr.io/no-star-4
+    sync:
+      'public/A/d.html': /www
+  - image: gcr.io/single-star-1
+    sync:
+      'public/*': /app
+  - image: gcr.io/single-star-2
+    sync:
+      'main*.js': /app
+  - image: gcr.io/single-star-3
+    sync:
+      '/public/b/*.js': /app
+  - image: gcr.io/single-star-4
+    sync:
+      '/c/prefix-*': /app
   - image: gcr.io/k8s-skaffold/node-example
     sync:
       '**/*.js': .
-  - image: gcr.io/k8s-skaffold/leeroy
   - image: gcr.io/k8s-skaffold/react-reload
     sync:
       'src/***/*.js': app/
@@ -158,12 +181,57 @@ apiVersion: skaffold/v1beta10
 kind: Config
 build:
   artifacts:
+  - image: gcr.io/no-star-1
+    sync:
+      manual:
+      - src: /public/A/B/a.html
+        dest: /www
+        strip: /public/A/B/
+  - image: gcr.io/no-star-2
+    sync:
+      manual:
+      - src: /b.html
+        dest: /www
+        strip: /
+  - image: gcr.io/no-star-3
+    sync:
+      manual:
+      - src: c.html
+        dest: /www
+  - image: gcr.io/no-star-4
+    sync:
+      manual:
+      - src: public/A/d.html
+        dest: /www
+        strip: public/A/
+  - image: gcr.io/single-star-1
+    sync:
+      manual:
+      - src: 'public/*'
+        dest: /app
+        strip: public/
+  - image: gcr.io/single-star-2
+    sync:
+      manual:
+      - src: 'main*.js'
+        dest: /app
+  - image: gcr.io/single-star-3
+    sync:
+      manual:
+      - src: '/public/b/*.js'
+        dest: /app
+        strip: /public/b/
+  - image: gcr.io/single-star-4
+    sync:
+      manual:
+      - src: '/c/prefix-*'
+        dest: /app
+        strip: /c/
   - image: gcr.io/k8s-skaffold/node-example
     sync:
       manual:
       - src: '**/*.js'
         dest: .
-  - image: gcr.io/k8s-skaffold/leeroy
   - image: gcr.io/k8s-skaffold/react-reload
     sync:
       manual: