diff --git a/rules/rules.go b/rules/rules.go
index 7c6ef11b..71f66930 100644
--- a/rules/rules.go
+++ b/rules/rules.go
@@ -31,7 +31,16 @@ func (r *Rule) Matches(path string) bool {
 		return r.Regexp.MatchString(path)
 	}
 
-	return strings.HasPrefix(path, r.Path)
+	if path == r.Path {
+		return true
+	}
+
+	prefix := r.Path
+	if prefix != "/" && !strings.HasSuffix(prefix, "/") {
+		prefix += "/"
+	}
+
+	return strings.HasPrefix(path, prefix)
 }
 
 // Regexp is a wrapper to the native regexp type where we
diff --git a/rules/rules_test.go b/rules/rules_test.go
index 570f921f..3046a2bd 100644
--- a/rules/rules_test.go
+++ b/rules/rules_test.go
@@ -2,6 +2,37 @@ package rules
 
 import "testing"
 
+func TestRuleMatches(t *testing.T) {
+	t.Parallel()
+
+	cases := []struct {
+		name     string
+		rulePath string
+		testPath string
+		want     bool
+	}{
+		{"exact match", "/uploads", "/uploads", true},
+		{"child path", "/uploads", "/uploads/file.txt", true},
+		{"sibling prefix", "/uploads", "/uploads_backup/secret.txt", false},
+		{"root rule", "/", "/anything", true},
+		{"trailing slash rule", "/uploads/", "/uploads/file.txt", true},
+		{"trailing slash no sibling", "/uploads/", "/uploads_backup/file.txt", false},
+		{"nested child", "/data/shared", "/data/shared/docs/file.txt", true},
+		{"nested sibling", "/data/shared", "/data/shared_private/file.txt", false},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+			r := &Rule{Path: tc.rulePath}
+			got := r.Matches(tc.testPath)
+			if got != tc.want {
+				t.Errorf("Rule{Path: %q}.Matches(%q) = %v; want %v", tc.rulePath, tc.testPath, got, tc.want)
+			}
+		})
+	}
+}
+
 func TestMatchHidden(t *testing.T) {
 	cases := map[string]bool{
 		"/":                   false,