diff --git a/pkg/build/stage/dependencies.go b/pkg/build/stage/dependencies.go
index 1b6f79d16d..318d2fa5ca 100644
--- a/pkg/build/stage/dependencies.go
+++ b/pkg/build/stage/dependencies.go
@@ -339,7 +339,7 @@ func generateChecksumCommand(from string, includePaths, excludePaths []string, r
 
 	var nameIncludeArgs []string
 	for _, includePath := range includePaths {
-		formattedPath := formatIncludeAndExcludePath(includePath)
+		formattedPath := util.SafeTrimGlobsAndSlashesFromPath(includePath)
 		nameIncludeArgs = append(
 			nameIncludeArgs,
 			fmt.Sprintf("-wholename \"%s\"", path.Join(from, formattedPath)),
@@ -353,7 +353,7 @@ func generateChecksumCommand(from string, includePaths, excludePaths []string, r
 
 	var nameExcludeArgs []string
 	for _, excludePath := range excludePaths {
-		formattedPath := formatIncludeAndExcludePath(excludePath)
+		formattedPath := util.SafeTrimGlobsAndSlashesFromPath(excludePath)
 		nameExcludeArgs = append(
 			nameExcludeArgs,
 			fmt.Sprintf("! -wholename \"%s\"", path.Join(from, formattedPath)),
@@ -388,10 +388,6 @@ func generateChecksumCommand(from string, includePaths, excludePaths []string, r
 	return command
 }
 
-func formatIncludeAndExcludePath(path string) string {
-	return strings.TrimRight(path, "*/")
-}
-
 func getDependencyImportID(dependencyImport *config.DependencyImport) string {
 	return util.Sha256Hash(
 		"Type", string(dependencyImport.Type),
diff --git a/pkg/path_matcher/common.go b/pkg/path_matcher/common.go
index 5933af912d..c264dce31e 100644
--- a/pkg/path_matcher/common.go
+++ b/pkg/path_matcher/common.go
@@ -46,7 +46,7 @@ func hasUniversalGlob(globs []string) bool {
 			return true
 		}
 
-		if trimRightAsterisks(glob) == "" {
+		if util.SafeTrimGlobsAndSlashesFromFilepath(glob) == "" {
 			return true
 		}
 	}
@@ -70,8 +70,8 @@ func isPathMatched(filePath, glob string) bool {
 	// The previous glob with the universal part `**/*` (path/*/dir/**/*).
 	for _, g := range []string{
 		glob,
-		trimRightAsterisks(glob),
-		filepath.Join(trimRightAsterisks(glob), "**", "*"),
+		util.SafeTrimGlobsAndSlashesFromFilepath(glob),
+		filepath.Join(util.SafeTrimGlobsAndSlashesFromFilepath(glob), "**", "*"),
 	} {
 		matched, err := doublestar.PathMatch(g, filePath)
 		if err != nil {
@@ -86,10 +86,6 @@ func isPathMatched(filePath, glob string) bool {
 	return false
 }
 
-func trimRightAsterisks(pattern string) string {
-	return strings.TrimRight(pattern, "*\\/")
-}
-
 func formatPaths(paths []string) []string {
 	var result []string
 	for _, path := range paths {
diff --git a/pkg/util/path.go b/pkg/util/path.go
index 73b81a9c28..7d0122133d 100644
--- a/pkg/util/path.go
+++ b/pkg/util/path.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"os"
 	"os/user"
+	"path"
 	"path/filepath"
 	"runtime"
 	"strings"
@@ -151,3 +152,23 @@ func FilepathsWithParents(path string) []string {
 
 	return res
 }
+
+// SafeTrimGlobsAndSlashesFromFilepath trims any trailing globs and/or slashes from the path,
+// while ignoring globs that are part of a directory or file name.
+func SafeTrimGlobsAndSlashesFromFilepath(p string) string {
+	return filepath.FromSlash(SafeTrimGlobsAndSlashesFromPath(p))
+}
+
+func SafeTrimGlobsAndSlashesFromPath(p string) string {
+	parts := SplitFilepath(p)
+	for i := len(parts) - 1; i >= 0; i-- {
+		if partWOGlobs := strings.TrimRight(parts[i], "*"); partWOGlobs != "" {
+			parts = parts[:i+1]
+			break
+		} else {
+			parts = parts[:i]
+		}
+	}
+
+	return path.Join(parts...)
+}
diff --git a/pkg/util/path_test.go b/pkg/util/path_test.go
new file mode 100644
index 0000000000..5c113f9d2c
--- /dev/null
+++ b/pkg/util/path_test.go
@@ -0,0 +1,57 @@
+package util
+
+import (
+	"testing"
+)
+
+func TestSafeTrimGlobsAndSlashes(t *testing.T) {
+	tests := []struct {
+		name string
+		path string
+		want string
+	}{
+		{
+			name: "globs",
+			path: "**/*",
+			want: "",
+		},
+		{
+			name: "empty path",
+			path: "",
+			want: "",
+		},
+		{
+			name: "path",
+			path: "path",
+			want: "path",
+		},
+		{
+			name: "path with trailing slash",
+			path: "path/",
+			want: "path",
+		},
+		{
+			name: "path with globs and slashes",
+			path: "path/**/*",
+			want: "path",
+		},
+		{
+			name: "path with glob as part of a directory or file name 1",
+			path: "path/name-*",
+			want: "path/name-*",
+		},
+		{
+			name: "path with glob as part of a directory or file name 2",
+			path: "path/*.tmp",
+			want: "path/*.tmp",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			if got := SafeTrimGlobsAndSlashesFromPath(tt.path); got != tt.want {
+				t.Errorf("SafeTrimGlobsAndSlashesFromPath() = %v, want %v", got, tt.want)
+			}
+		})
+	}
+}