diff --git a/client/internal/engine.go b/client/internal/engine.go
index 1abb8163d..079adf7e8 100644
--- a/client/internal/engine.go
+++ b/client/internal/engine.go
@@ -1968,21 +1968,24 @@ func (e *Engine) toExcludedLazyPeers(rules []firewallManager.ForwardRule, peers
 }
 
 // isChecksEqual checks if two slices of checks are equal.
-func isChecksEqual(checks []*mgmProto.Checks, oChecks []*mgmProto.Checks) bool {
-	for _, check := range checks {
-		sort.Slice(check.Files, func(i, j int) bool {
-			return check.Files[i] < check.Files[j]
-		})
-	}
-	for _, oCheck := range oChecks {
-		sort.Slice(oCheck.Files, func(i, j int) bool {
-			return oCheck.Files[i] < oCheck.Files[j]
-		})
+func isChecksEqual(checks1, checks2 []*mgmProto.Checks) bool {
+	normalize := func(checks []*mgmProto.Checks) []string {
+		normalized := make([]string, len(checks))
+
+		for i, check := range checks {
+			sortedFiles := slices.Clone(check.Files)
+			sort.Strings(sortedFiles)
+			normalized[i] = strings.Join(sortedFiles, "|")
+		}
+
+		sort.Strings(normalized)
+		return normalized
 	}
 
-	return slices.EqualFunc(checks, oChecks, func(checks, oChecks *mgmProto.Checks) bool {
-		return slices.Equal(checks.Files, oChecks.Files)
-	})
+	n1 := normalize(checks1)
+	n2 := normalize(checks2)
+
+	return slices.Equal(n1, n2)
 }
 
 func getInterfacePrefixes() ([]netip.Prefix, error) {
diff --git a/client/internal/engine_test.go b/client/internal/engine_test.go
index f02138686..fffbed533 100644
--- a/client/internal/engine_test.go
+++ b/client/internal/engine_test.go
@@ -1270,6 +1270,82 @@ func Test_CheckFilesEqual(t *testing.T) {
 			},
 			expectedBool: false,
 		},
+		{
+			name: "Compared Slices with same files but different order should return true",
+			inputChecks1: []*mgmtProto.Checks{
+				{
+					Files: []string{
+						"testfile1",
+						"testfile2",
+					},
+				},
+				{
+					Files: []string{
+						"testfile4",
+						"testfile3",
+					},
+				},
+			},
+			inputChecks2: []*mgmtProto.Checks{
+				{
+					Files: []string{
+						"testfile3",
+						"testfile4",
+					},
+				},
+				{
+					Files: []string{
+						"testfile2",
+						"testfile1",
+					},
+				},
+			},
+			expectedBool: true,
+		},
+		{
+			name: "Compared Slices with same files but different order while first is equal should return true",
+			inputChecks1: []*mgmtProto.Checks{
+				{
+					Files: []string{
+						"testfile0",
+						"testfile1",
+					},
+				},
+				{
+					Files: []string{
+						"testfile0",
+						"testfile2",
+					},
+				},
+				{
+					Files: []string{
+						"testfile0",
+						"testfile3",
+					},
+				},
+			},
+			inputChecks2: []*mgmtProto.Checks{
+				{
+					Files: []string{
+						"testfile0",
+						"testfile1",
+					},
+				},
+				{
+					Files: []string{
+						"testfile0",
+						"testfile3",
+					},
+				},
+				{
+					Files: []string{
+						"testfile0",
+						"testfile2",
+					},
+				},
+			},
+			expectedBool: true,
+		},
 	}
 	for _, testCase := range testCases {
 		t.Run(testCase.name, func(t *testing.T) {