diff --git a/pkg/ignore/rules.go b/pkg/ignore/rules.go
index a8160da2a..108bb6b29 100644
--- a/pkg/ignore/rules.go
+++ b/pkg/ignore/rules.go
@@ -85,8 +85,9 @@ func Parse(file io.Reader) (*Rules, error) {
 
 // Ignore evaluates the file at the given path, and returns true if it should be ignored.
 //
-// Ignore evaluates path against the rules in order. Evaluation stops when a match
-// is found. Matching a negative rule will stop evaluation.
+// Ignore evaluates path against all rules in order. Later rules can override earlier ones,
+// following gitignore semantics where negation patterns (starting with !) can re-include
+// previously excluded files.
 func (r *Rules) Ignore(path string, fi os.FileInfo) bool {
 	// Don't match on empty dirs.
 	if path == "" {
@@ -99,34 +100,30 @@ func (r *Rules) Ignore(path string, fi os.FileInfo) bool {
 	if path == "." || path == "./" {
 		return false
 	}
+
+	// Track whether the file should be ignored. Start with false (not ignored),
+	// and let each matching rule update this value. The last matching rule wins.
+	ignored := false
+
 	for _, p := range r.patterns {
 		if p.match == nil {
 			slog.Info("this will be ignored no matcher supplied", "patterns", p.raw)
 			return false
 		}
 
-		// For negative rules, we need to capture and return non-matches,
-		// and continue for matches.
-		if p.negate {
-			if p.mustDir && !fi.IsDir() {
-				return true
-			}
-			if !p.match(path, fi) {
-				return true
-			}
-			continue
-		}
-
 		// If the rule is looking for directories, and this is not a directory,
 		// skip it.
 		if p.mustDir && !fi.IsDir() {
 			continue
 		}
+
 		if p.match(path, fi) {
-			return true
+			// For negation rules, matching means "don't ignore this file"
+			// For regular rules, matching means "ignore this file"
+			ignored = !p.negate
 		}
 	}
-	return false
+	return ignored
 }
 
 // parseRule parses a rule string and creates a pattern, which is then stored in the Rules object.
diff --git a/pkg/ignore/rules_test.go b/pkg/ignore/rules_test.go
index 9581cf09f..df318b4cb 100644
--- a/pkg/ignore/rules_test.go
+++ b/pkg/ignore/rules_test.go
@@ -112,11 +112,11 @@ func TestIgnore(t *testing.T) {
 		{`cargo/`, "mast/", false},
 		{`helm.txt/`, "helm.txt", false},
 
-		// Negation tests
+		// Negation tests (single pattern - negation alone doesn't ignore non-matches)
 		{`!helm.txt`, "helm.txt", false},
-		{`!helm.txt`, "tiller.txt", true},
-		{`!*.txt`, "cargo", true},
-		{`!cargo/`, "mast/", true},
+		{`!helm.txt`, "tiller.txt", false},
+		{`!*.txt`, "cargo", false},
+		{`!cargo/`, "mast/", false},
 
 		// Absolute path tests
 		{`/a.txt`, "a.txt", true},
@@ -149,6 +149,87 @@ func TestAddDefaults(t *testing.T) {
 	}
 }
 
+func TestNegationPatterns(t *testing.T) {
+	// Test multi-rule scenarios with negation patterns (gitignore semantics)
+	tests := []struct {
+		name     string
+		rules    string
+		file     string
+		expected bool
+	}{
+		// Basic negation: *.txt ignored, but README.txt is un-ignored
+		{
+			name:     "negation re-includes previously excluded file",
+			rules:    "*.txt\n!helm.txt",
+			file:     "helm.txt",
+			expected: false, // Should NOT be ignored (negation re-includes it)
+		},
+		{
+			name:     "file matching exclusion but not negation is ignored",
+			rules:    "*.txt\n!helm.txt",
+			file:     "tiller.txt",
+			expected: true, // Should be ignored (matches *.txt, doesn't match negation)
+		},
+		{
+			name:     "unrelated file is not affected by negation",
+			rules:    "*.txt\n!helm.txt",
+			file:     "cargo",
+			expected: false, // Should NOT be ignored (doesn't match *.txt)
+		},
+		// Multiple negations
+		{
+			name:     "multiple negations - first negated file",
+			rules:    "*.txt\n!helm.txt\n!tiller.txt",
+			file:     "helm.txt",
+			expected: false,
+		},
+		{
+			name:     "multiple negations - second negated file",
+			rules:    "*.txt\n!helm.txt\n!tiller.txt",
+			file:     "tiller.txt",
+			expected: false,
+		},
+		{
+			name:     "multiple negations - non-negated file still ignored",
+			rules:    "*.txt\n!helm.txt\n!tiller.txt",
+			file:     "rudder.txt",
+			expected: true,
+		},
+		// Negation pattern alone should not ignore anything
+		{
+			name:     "negation alone does not ignore non-matching files",
+			rules:    "!helm.txt",
+			file:     "tiller.txt",
+			expected: false,
+		},
+		{
+			name:     "negation alone explicitly un-ignores matching files",
+			rules:    "!helm.txt",
+			file:     "helm.txt",
+			expected: false,
+		},
+	}
+
+	for _, test := range tests {
+		t.Run(test.name, func(t *testing.T) {
+			r, err := parseString(test.rules)
+			if err != nil {
+				t.Fatalf("Failed to parse rules: %s", err)
+			}
+			fi, err := os.Stat(filepath.Join(testdata, test.file))
+			if err != nil {
+				t.Fatalf("Fixture missing: %s", err)
+			}
+
+			result := r.Ignore(test.file, fi)
+			if result != test.expected {
+				t.Errorf("Expected Ignore(%q) to be %v for rules %q, got %v",
+					test.file, test.expected, test.rules, result)
+			}
+		})
+	}
+}
+
 func parseString(str string) (*Rules, error) {
 	b := bytes.NewBuffer([]byte(str))
 	return Parse(b)