diff --git a/server/src/service/network/AdvancedMatcher.ts b/server/src/service/network/AdvancedMatcher.ts
index 8b25c53e8..8e77ef3ec 100644
--- a/server/src/service/network/AdvancedMatcher.ts
+++ b/server/src/service/network/AdvancedMatcher.ts
@@ -1,5 +1,6 @@
 import { Monitor } from "@/domain/monitors/monitor.types.js";
 import jmespath from "jmespath";
+import RE2 from "re2";
 type JmesPath = typeof jmespath;
 
 export interface IAdvancedMatcher {
@@ -9,13 +10,6 @@ export interface IAdvancedMatcher {
 export class AdvancedMatcher implements IAdvancedMatcher {
 	constructor(private jmespath: JmesPath) {}
 
-	private compare(actual: unknown, expected: string, method?: string): boolean {
-		if (method === "equal") return String(actual) === expected;
-		if (method === "include") return String(actual).includes(expected);
-		if (method === "regex") return new RegExp(expected).test(String(actual));
-		return String(actual) === expected; // Default
-	}
-
 	validate<T>(payload: T, monitor: Monitor): { ok: boolean; message: string; extracted?: T | undefined } {
 		const { useAdvancedMatching, jsonPath, matchMethod, expectedValue } = monitor;
 		if (!useAdvancedMatching) return { ok: true, message: "Success" };
@@ -30,19 +24,38 @@ export class AdvancedMatcher implements IAdvancedMatcher {
 			}
 		}
 
-		if (expectedValue) {
-			const ok = this.compare(dataToValidate, expectedValue, matchMethod);
+		if (!expectedValue) {
+			const isFalsy = dataToValidate === false || dataToValidate === "false" || dataToValidate === undefined || dataToValidate === null;
 			return {
-				ok,
-				message: ok ? "Success" : "Expected value did not match",
+				ok: !isFalsy,
+				message: !isFalsy ? "Success" : "Extracted value is falsy",
 				extracted: dataToValidate,
 			};
 		}
 
-		const isFalsy = dataToValidate === false || dataToValidate === "false" || dataToValidate === undefined || dataToValidate === null;
+		let actual: string;
+		try {
+			actual = String(dataToValidate);
+		} catch {
+			return { ok: false, message: "Error evaluating response value", extracted: dataToValidate };
+		}
+
+		let ok: boolean;
+		if (matchMethod === "include") {
+			ok = actual.includes(expectedValue);
+		} else if (matchMethod === "regex") {
+			try {
+				ok = new RE2(expectedValue).test(actual);
+			} catch {
+				return { ok: false, message: "Invalid regex pattern", extracted: dataToValidate };
+			}
+		} else {
+			ok = actual === expectedValue;
+		}
+
 		return {
-			ok: !isFalsy,
-			message: !isFalsy ? "Success" : "Extracted value is falsy",
+			ok,
+			message: ok ? "Success" : "Expected value did not match",
 			extracted: dataToValidate,
 		};
 	}