diff --git a/server/package-lock.json b/server/package-lock.json
index 9255f9889..726759967 100644
--- a/server/package-lock.json
+++ b/server/package-lock.json
@@ -36,6 +36,7 @@
 				"multer": "^1.4.5-lts.2",
 				"nodemailer": "8.0.5",
 				"ping": "0.4.4",
+				"re2": "^1.24.1",
 				"sharp": "0.33.5",
 				"ssl-checker": "2.0.10",
 				"swagger-ui-express": "5.0.1",
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 			"license": "MIT",
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@@ -1493,7 +1493,6 @@
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@@ -1538,7 +1537,6 @@
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@@ -1554,6 +1552,29 @@
 				"kuler": "^2.0.0"
 			}
 		},
+		"node_modules/@emnapi/core": {
+			"version": "1.11.2",
+			"resolved": "https://registry.npmjs.org/@emnapi/core/-/core-1.11.2.tgz",
+			"integrity": "sha512-TC8MkTuZUtcTSiFeuC0ksCh9QIJ5+F21MvZ4Wn4ORfYaFJ/0dsiudv5tVkejgwZlwQ39jL9WWDe2lz8x0WglOA==",
+			"dev": true,
+			"license": "MIT",
+			"optional": true,
+			"peer": true,
+			"dependencies": {
+				"@emnapi/wasi-threads": "1.2.2",
+				"tslib": "^2.4.0"
+			}
+		},
+		"node_modules/@emnapi/runtime": {
+			"version": "1.11.2",
+			"resolved": "https://registry.npmjs.org/@emnapi/runtime/-/runtime-1.11.2.tgz",
+			"integrity": "sha512-kyOl3X0DuTiT1h2ft8r2fYO8JYtU9a9Xis/zBSiGArNaagCOWx90N1k2wxp18czFDH+OgcWGb5ZP/XMt3dcyPA==",
+			"license": "MIT",
+			"optional": true,
+			"dependencies": {
+				"tslib": "^2.4.0"
+			}
+		},
 		"node_modules/@emnapi/wasi-threads": {
 			"version": "1.2.2",
 			"resolved": "https://registry.npmjs.org/@emnapi/wasi-threads/-/wasi-threads-1.2.2.tgz",
@@ -1561,6 +1582,7 @@
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 			"license": "MIT",
 			"optional": true,
+			"peer": true,
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 				"tslib": "^2.4.0"
 			}
@@ -2625,6 +2647,18 @@
 				"node": ">=12"
 			}
 		},
+		"node_modules/@isaacs/fs-minipass": {
+			"version": "4.0.1",
+			"resolved": "https://registry.npmjs.org/@isaacs/fs-minipass/-/fs-minipass-4.0.1.tgz",
+			"integrity": "sha512-wgm9Ehl2jpeqP3zw/7mo3kRHFp5MEDhqAdwy1fTGkHAwnkGOVsgpvQhL8B5n1qlb01jV3n/bI0ZfZp5lWA1k4w==",
+			"license": "ISC",
+			"dependencies": {
+				"minipass": "^7.0.4"
+			},
+			"engines": {
+				"node": ">=18.0.0"
+			}
+		},
 		"node_modules/@istanbuljs/load-nyc-config": {
 			"version": "1.1.0",
 			"resolved": "https://registry.npmjs.org/@istanbuljs/load-nyc-config/-/load-nyc-config-1.1.0.tgz",
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 			"dev": true,
 			"license": "MIT",
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 				"@typescript-eslint/types": "8.56.1",
@@ -5277,6 +5308,15 @@
 				"win32"
 			]
 		},
+		"node_modules/abbrev": {
+			"version": "4.0.0",
+			"resolved": "https://registry.npmjs.org/abbrev/-/abbrev-4.0.0.tgz",
+			"integrity": "sha512-a1wflyaL0tHtJSmLSOVybYhy22vRih4eduhhrkcjgrWGnRfrZtovJ2FRjxuTtkkj47O/baf0R86QU5OuYpz8fA==",
+			"license": "ISC",
+			"engines": {
+				"node": "^20.17.0 || >=22.9.0"
+			}
+		},
 		"node_modules/accepts": {
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 			"resolved": "https://registry.npmjs.org/accepts/-/accepts-1.3.8.tgz",
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 			"license": "MIT",
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@@ -5712,7 +5751,6 @@
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 			"dev": true,
 			"license": "Apache-2.0",
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@@ -6033,7 +6071,6 @@
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@@ -6913,7 +6950,6 @@
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 			"dependencies": {
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@@ -7631,7 +7667,6 @@
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 				"@eslint-community/eslint-utils": "^4.8.0",
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@@ -7998,12 +8033,17 @@
 				"node": "^18.14.0 || ^20.0.0 || ^22.0.0 || >=24.0.0"
 			}
 		},
+		"node_modules/exponential-backoff": {
+			"version": "3.1.3",
+			"resolved": "https://registry.npmjs.org/exponential-backoff/-/exponential-backoff-3.1.3.tgz",
+			"integrity": "sha512-ZgEeZXj30q+I0EN+CbSSpIyPaJ5HVQD18Z1m+u1FXbAeT94mr1zw50q4q6jiiC447Nl/YTcIYSAftiGqetwXCA==",
+			"license": "Apache-2.0"
+		},
 		"node_modules/express": {
 			"version": "4.22.2",
 			"resolved": "https://registry.npmjs.org/express/-/express-4.22.2.tgz",
 			"integrity": "sha512-IuL+Elrou2ZvCFHs18/CIzy2Nzvo25nZ1/D2eIZlz7c+QUayAcYoiM2BthCjs+EBHVpjYjcuLDAiCWgeIX3X1Q==",
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@@ -8911,7 +8951,6 @@
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-			"dev": true,
 			"license": "ISC"
 		},
 		"node_modules/handlebars": {
@@ -9262,6 +9301,19 @@
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 			"license": "ISC"
 		},
+		"node_modules/install-artifact-from-github": {
+			"version": "1.6.0",
+			"resolved": "https://registry.npmjs.org/install-artifact-from-github/-/install-artifact-from-github-1.6.0.tgz",
+			"integrity": "sha512-wKsuzN8fy8QK7iEUqyWTQmvZ1QFGPn1xyl3/1iIIDthDjS7Hn9HoPwHlNakZirWbCsbad0lZMkr6Xfbpe1pUzw==",
+			"license": "BSD-3-Clause",
+			"bin": {
+				"install-from-cache": "bin/install-from-cache.js",
+				"save-to-github-cache": "bin/save-to-github-cache.js"
+			},
+			"engines": {
+				"node": ">=18"
+			}
+		},
 		"node_modules/ip-address": {
 			"version": "10.2.0",
 			"resolved": "https://registry.npmjs.org/ip-address/-/ip-address-10.2.0.tgz",
@@ -9692,7 +9744,6 @@
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 			"dev": true,
 			"license": "MIT",
-			"peer": true,
 			"dependencies": {
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 				"@jest/types": "30.4.1",
@@ -11199,6 +11250,18 @@
 				"node": ">=16 || 14 >=14.17"
 			}
 		},
+		"node_modules/minizlib": {
+			"version": "3.1.0",
+			"resolved": "https://registry.npmjs.org/minizlib/-/minizlib-3.1.0.tgz",
+			"integrity": "sha512-KZxYo1BUkWD2TVFLr0MQoM8vUUigWD3LlD83a/75BqC+4qE0Hb1Vo5v1FgcfaNXvfXzr+5EhQ6ing/CaBijTlw==",
+			"license": "MIT",
+			"dependencies": {
+				"minipass": "^7.1.2"
+			},
+			"engines": {
+				"node": ">= 18"
+			}
+		},
 		"node_modules/mjml": {
 			"version": "5.0.0-alpha.6",
 			"resolved": "https://registry.npmjs.org/mjml/-/mjml-5.0.0-alpha.6.tgz",
@@ -11952,8 +12015,7 @@
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 			"resolved": "https://registry.npmjs.org/nan/-/nan-2.27.0.tgz",
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-			"license": "MIT",
-			"optional": true
+			"license": "MIT"
 		},
 		"node_modules/nano-spawn": {
 			"version": "2.0.0",
@@ -12099,6 +12161,54 @@
 				"webidl-conversions": "^3.0.0"
 			}
 		},
+		"node_modules/node-gyp": {
+			"version": "12.4.0",
+			"resolved": "https://registry.npmjs.org/node-gyp/-/node-gyp-12.4.0.tgz",
+			"integrity": "sha512-OMcPNvqTCFUnNaBlmdgq+lfNqY7gTiSmNRDjY3uAXRyudeKZEZxu3CLtjMQrx4zZxCX2b/mpNqTtwuCJgXhHkw==",
+			"license": "MIT",
+			"dependencies": {
+				"env-paths": "^2.2.0",
+				"exponential-backoff": "^3.1.1",
+				"graceful-fs": "^4.2.6",
+				"nopt": "^9.0.0",
+				"proc-log": "^6.0.0",
+				"semver": "^7.3.5",
+				"tar": "^7.5.4",
+				"tinyglobby": "^0.2.12",
+				"undici": "^6.25.0",
+				"which": "^6.0.0"
+			},
+			"bin": {
+				"node-gyp": "bin/node-gyp.js"
+			},
+			"engines": {
+				"node": "^20.17.0 || >=22.9.0"
+			}
+		},
+		"node_modules/node-gyp/node_modules/isexe": {
+			"version": "4.0.0",
+			"resolved": "https://registry.npmjs.org/isexe/-/isexe-4.0.0.tgz",
+			"integrity": "sha512-FFUtZMpoZ8RqHS3XeXEmHWLA4thH+ZxCv2lOiPIn1Xc7CxrqhWzNSDzD+/chS/zbYezmiwWLdQC09JdQKmthOw==",
+			"license": "BlueOak-1.0.0",
+			"engines": {
+				"node": ">=20"
+			}
+		},
+		"node_modules/node-gyp/node_modules/which": {
+			"version": "6.0.1",
+			"resolved": "https://registry.npmjs.org/which/-/which-6.0.1.tgz",
+			"integrity": "sha512-oGLe46MIrCRqX7ytPUf66EAYvdeMIZYn3WaocqqKZAxrBpkqHfL/qvTyJ/bTk5+AqHCjXmrv3CEWgy368zhRUg==",
+			"license": "ISC",
+			"dependencies": {
+				"isexe": "^4.0.0"
+			},
+			"bin": {
+				"node-which": "bin/which.js"
+			},
+			"engines": {
+				"node": "^20.17.0 || >=22.9.0"
+			}
+		},
 		"node_modules/node-int64": {
 			"version": "0.4.0",
 			"resolved": "https://registry.npmjs.org/node-int64/-/node-int64-0.4.0.tgz",
@@ -12173,6 +12283,21 @@
 				"node": ">=4"
 			}
 		},
+		"node_modules/nopt": {
+			"version": "9.0.0",
+			"resolved": "https://registry.npmjs.org/nopt/-/nopt-9.0.0.tgz",
+			"integrity": "sha512-Zhq3a+yFKrYwSBluL4H9XP3m3y5uvQkB/09CwDruCiRmR/UJYnn9W4R48ry0uGC70aeTPKLynBtscP9efFFcPw==",
+			"license": "ISC",
+			"dependencies": {
+				"abbrev": "^4.0.0"
+			},
+			"bin": {
+				"nopt": "bin/nopt.js"
+			},
+			"engines": {
+				"node": "^20.17.0 || >=22.9.0"
+			}
+		},
 		"node_modules/normalize-path": {
 			"version": "3.0.0",
 			"resolved": "https://registry.npmjs.org/normalize-path/-/normalize-path-3.0.0.tgz",
@@ -12709,7 +12834,6 @@
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-			"peer": true,
 			"dependencies": {
 				"nanoid": "^3.3.11",
 				"picocolors": "^1.1.1",
@@ -13367,6 +13491,15 @@
 				"url": "https://github.com/chalk/ansi-styles?sponsor=1"
 			}
 		},
+		"node_modules/proc-log": {
+			"version": "6.1.0",
+			"resolved": "https://registry.npmjs.org/proc-log/-/proc-log-6.1.0.tgz",
+			"integrity": "sha512-iG+GYldRf2BQ0UDUAd6JQ/RwzaQy6mXmsk/IzlYyal4A4SNFw54MeH4/tLkF4I5WoWG9SQwuqWzS99jaFQHBuQ==",
+			"license": "ISC",
+			"engines": {
+				"node": "^20.17.0 || >=22.9.0"
+			}
+		},
 		"node_modules/process-nextick-args": {
 			"version": "2.0.1",
 			"resolved": "https://registry.npmjs.org/process-nextick-args/-/process-nextick-args-2.0.1.tgz",
@@ -13579,6 +13712,24 @@
 				"node": ">= 0.8"
 			}
 		},
+		"node_modules/re2": {
+			"version": "1.24.1",
+			"resolved": "https://registry.npmjs.org/re2/-/re2-1.24.1.tgz",
+			"integrity": "sha512-uRl9cLDKuobJQp+6lVz7E3AyVszubUJ0fqAMWout4ocUWTIFvdHgpqLwwMh/vuNGGGJGh2p2mJZJIQr9am9M/A==",
+			"hasInstallScript": true,
+			"license": "BSD-3-Clause",
+			"dependencies": {
+				"install-artifact-from-github": "^1.6.0",
+				"nan": "^2.27.0",
+				"node-gyp": "^12.3.0"
+			},
+			"engines": {
+				"node": ">=22"
+			},
+			"funding": {
+				"url": "https://github.com/sponsors/uhop"
+			}
+		},
 		"node_modules/react-is-18": {
 			"name": "react-is",
 			"version": "18.3.1",
@@ -14639,6 +14790,22 @@
 				"url": "https://opencollective.com/synckit"
 			}
 		},
+		"node_modules/tar": {
+			"version": "7.5.19",
+			"resolved": "https://registry.npmjs.org/tar/-/tar-7.5.19.tgz",
+			"integrity": "sha512-4LeEWl96twnS2Q7Bz4MGqgazLqO+hJN63GZxXoIqh1T3VweYD997gbU1ItNsQafqqXTXd5WFyFdReLtwvRBNiw==",
+			"license": "BlueOak-1.0.0",
+			"dependencies": {
+				"@isaacs/fs-minipass": "^4.0.0",
+				"chownr": "^3.0.0",
+				"minipass": "^7.1.2",
+				"minizlib": "^3.1.0",
+				"yallist": "^5.0.0"
+			},
+			"engines": {
+				"node": ">=18"
+			}
+		},
 		"node_modules/tar-fs": {
 			"version": "2.1.4",
 			"resolved": "https://registry.npmjs.org/tar-fs/-/tar-fs-2.1.4.tgz",
@@ -14667,6 +14834,24 @@
 				"node": ">=6"
 			}
 		},
+		"node_modules/tar/node_modules/chownr": {
+			"version": "3.0.0",
+			"resolved": "https://registry.npmjs.org/chownr/-/chownr-3.0.0.tgz",
+			"integrity": "sha512-+IxzY9BZOQd/XuYPRmrvEVjF/nqj5kgT4kEq7VofrDoM1MxoRjEWkrCC3EtLi59TVawxTAn+orJwFQcrqEN1+g==",
+			"license": "BlueOak-1.0.0",
+			"engines": {
+				"node": ">=18"
+			}
+		},
+		"node_modules/tar/node_modules/yallist": {
+			"version": "5.0.0",
+			"resolved": "https://registry.npmjs.org/yallist/-/yallist-5.0.0.tgz",
+			"integrity": "sha512-YgvUTfwqyc7UXVMrB+SImsVYSmTS8X/tSrtdNZMImM+n7+QTriRXyXim0mBrTXNeqzVF0KWGgHPeiyViFFrNDw==",
+			"license": "BlueOak-1.0.0",
+			"engines": {
+				"node": ">=18"
+			}
+		},
 		"node_modules/teex": {
 			"version": "1.0.1",
 			"resolved": "https://registry.npmjs.org/teex/-/teex-1.0.1.tgz",
@@ -14697,7 +14882,6 @@
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 			"resolved": "https://registry.npmjs.org/tinyglobby/-/tinyglobby-0.2.15.tgz",
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-			"dev": true,
 			"license": "MIT",
 			"dependencies": {
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@@ -14714,7 +14898,6 @@
 			"version": "6.5.0",
 			"resolved": "https://registry.npmjs.org/fdir/-/fdir-6.5.0.tgz",
 			"integrity": "sha512-tIbYtZbucOs0BRGqPJkshJUYdL+SDH7dVM8gjy+ERp3WAUjLEFJE+02kanyHtwjWOnwrKYBiwAmM0p4kLJAnXg==",
-			"dev": true,
 			"license": "MIT",
 			"engines": {
 				"node": ">=12.0.0"
@@ -14732,9 +14915,7 @@
 			"version": "4.0.4",
 			"resolved": "https://registry.npmjs.org/picomatch/-/picomatch-4.0.4.tgz",
 			"integrity": "sha512-QP88BAKvMam/3NxH6vj2o21R6MjxZUAd6nlwAS/pnGvN9IVLocLHxGYIzFhg6fUQ+5th6P4dv4eW9jX3DSIj7A==",
-			"dev": true,
 			"license": "MIT",
-			"peer": true,
 			"engines": {
 				"node": ">=12"
 			},
@@ -14903,7 +15084,6 @@
 			"integrity": "sha512-f0FFpIdcHgn8zcPSbf1dRevwt047YMnaiJM3u2w2RewrB+fob/zePZcrOyQoLMMO7aBIddLcQIEK5dYjkLnGrQ==",
 			"dev": true,
 			"license": "MIT",
-			"peer": true,
 			"dependencies": {
 				"@cspotcode/source-map-support": "^0.8.0",
 				"@tsconfig/node10": "^1.0.7",
@@ -15067,7 +15247,6 @@
 			"integrity": "sha512-CWBzXQrc/qOkhidw1OzBTQuYRbfyxDXJMVJ1XNwUHGROVmuaeiEm3OslpZ1RV96d7SKKjZKrSJu3+t/xlw3R9A==",
 			"devOptional": true,
 			"license": "Apache-2.0",
-			"peer": true,
 			"bin": {
 				"tsc": "bin/tsc",
 				"tsserver": "bin/tsserver"
@@ -15121,9 +15300,9 @@
 			"license": "MIT"
 		},
 		"node_modules/undici": {
-			"version": "6.24.1",
-			"resolved": "https://registry.npmjs.org/undici/-/undici-6.24.1.tgz",
-			"integrity": "sha512-sC+b0tB1whOCzbtlx20fx3WgCXwkW627p4EA9uM+/tNNPkSS+eSEld6pAs9nDv7WbY1UUljBMYPtu9BCOrCWKA==",
+			"version": "6.27.0",
+			"resolved": "https://registry.npmjs.org/undici/-/undici-6.27.0.tgz",
+			"integrity": "sha512-YmfV3YnEDzXRC5lZ2jWtWWHKGUm1zIt8AhesR1tens+HTNv+YZlN/dp6G727LOvMJ8xjP9Be7Y2Sdr96LDm+pg==",
 			"license": "MIT",
 			"engines": {
 				"node": ">=18.17"
@@ -15934,7 +16113,6 @@
 			"resolved": "https://registry.npmjs.org/zod/-/zod-4.3.6.tgz",
 			"integrity": "sha512-rftlrkhHZOcjDwkGlnUtZZkvaPHCsDATp4pGpuOOMDaTdDDXF91wuVDJoWoPsKX/3YPQ5fHuF3STjcYyKr+Qhg==",
 			"license": "MIT",
-			"peer": true,
 			"funding": {
 				"url": "https://github.com/sponsors/colinhacks"
 			}
diff --git a/server/package.json b/server/package.json
index f44dd7031..7c59d2b94 100755
--- a/server/package.json
+++ b/server/package.json
@@ -58,6 +58,7 @@
 		"multer": "^1.4.5-lts.2",
 		"nodemailer": "8.0.5",
 		"ping": "0.4.4",
+		"re2": "^1.24.1",
 		"sharp": "0.33.5",
 		"ssl-checker": "2.0.10",
 		"swagger-ui-express": "5.0.1",
diff --git a/server/src/api/validation/monitorValidation.ts b/server/src/api/validation/monitorValidation.ts
index 6dea5b856..e8bae9261 100644
--- a/server/src/api/validation/monitorValidation.ts
+++ b/server/src/api/validation/monitorValidation.ts
@@ -1,4 +1,5 @@
 import { z } from "zod";
+import RE2 from "re2";
 import { booleanCoercion, dnsHostnameRegex, dnsServerValidation } from "./shared.js";
 import { GeoContinents } from "@/domain/geo-checks/geo-check.type.js";
 import {
@@ -71,6 +72,20 @@ const refineStrategyType = (body: { type?: string; strategy?: string }, ctx: z.R
 	}
 };
 
+// The regex is executed at check time with RE2, reject patterns RE2 won't accept
+const refineRegexPattern = (body: { matchMethod?: string; expectedValue?: string }, ctx: z.RefinementCtx) => {
+	if (body.matchMethod !== "regex" || !body.expectedValue) return;
+	try {
+		new RE2(body.expectedValue);
+	} catch {
+		ctx.addIssue({
+			code: "custom",
+			path: ["expectedValue"],
+			message: "Invalid regex pattern. Backreferences and lookahead/lookbehind are not supported.",
+		});
+	}
+};
+
 const refineHeadMatching = (body: { method?: string; useAdvancedMatching?: boolean; jsonPath?: string }, ctx: z.RefinementCtx) => {
 	if (body.method === "HEAD" && (body.useAdvancedMatching === true || (body.jsonPath ?? "") !== "")) {
 		ctx.addIssue({
@@ -120,7 +135,8 @@ export const createMonitorBodyValidation = z
 	})
 	.superRefine(refineDnsHostname)
 	.superRefine(refineStrategyType)
-	.superRefine(refineHeadMatching);
+	.superRefine(refineHeadMatching)
+	.superRefine(refineRegexPattern);
 
 export const editMonitorBodyValidation = z
 	.object({
@@ -159,7 +175,8 @@ export const editMonitorBodyValidation = z
 	})
 	.superRefine(refineDnsHostname)
 	.superRefine(refineStrategyType)
-	.superRefine(refineHeadMatching);
+	.superRefine(refineHeadMatching)
+	.superRefine(refineRegexPattern);
 
 export const pauseMonitorParamValidation = z.object({
 	monitorId: z.string().min(1, "Monitor ID is required"),
@@ -232,7 +249,8 @@ const importedMonitorSchema = z
 	})
 	.superRefine(refineDnsHostname)
 	.superRefine(refineStrategyType)
-	.superRefine(refineHeadMatching);
+	.superRefine(refineHeadMatching)
+	.superRefine(refineRegexPattern);
 
 export const importMonitorsBodyValidation = z.object({
 	monitors: z.array(importedMonitorSchema).min(1, "At least one monitor is required"),
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,
 		};
 	}
diff --git a/server/test/unit/providers/network/advancedMatcher.test.ts b/server/test/unit/providers/network/advancedMatcher.test.ts
index f94e9bb53..2cfb3a7f0 100644
--- a/server/test/unit/providers/network/advancedMatcher.test.ts
+++ b/server/test/unit/providers/network/advancedMatcher.test.ts
@@ -119,6 +119,34 @@ describe("AdvancedMatcher", () => {
 				expect(result.ok).toBe(false);
 			});
 
+			it("returns a clear error when the regex pattern is rejected by RE2", () => {
+				const matcher = new AdvancedMatcher(createMockJmespath() as any);
+				const result = matcher.validate(
+					{ code: "200" },
+					// Backreferences are unsupported by RE2 and previously ReDoS-prone; RE2 throws on construction.
+					makeMonitor({ useAdvancedMatching: true, jsonPath: "code", matchMethod: "regex", expectedValue: "(a+)\\1" })
+				);
+
+				expect(result.ok).toBe(false);
+				expect(result.message).toBe("Invalid regex pattern");
+				expect(result.extracted).toBe("200");
+			});
+
+			it("returns a distinct error when the extracted value cannot be coerced to a string", () => {
+				// An object with a throwing toString/valueOf (like Object.create(null)) makes String() throw.
+				const unstringifiable = { toString: () => { throw new Error("nope"); } };
+				const jmespath = { search: jest.fn().mockReturnValue(unstringifiable) };
+				const matcher = new AdvancedMatcher(jmespath as any);
+
+				const result = matcher.validate(
+					{},
+					makeMonitor({ useAdvancedMatching: true, jsonPath: "field", matchMethod: "equal", expectedValue: "x" })
+				);
+
+				expect(result.ok).toBe(false);
+				expect(result.message).toBe("Error evaluating response value");
+			});
+
 			it("defaults to 'equal' comparison when matchMethod is undefined", () => {
 				const matcher = new AdvancedMatcher(createMockJmespath() as any);
 				const result = matcher.validate({ val: "exact" }, makeMonitor({ useAdvancedMatching: true, jsonPath: "val", expectedValue: "exact" }));
diff --git a/server/test/unit/validation/monitorValidation.test.ts b/server/test/unit/validation/monitorValidation.test.ts
index d7a68b00b..d6998367a 100644
--- a/server/test/unit/validation/monitorValidation.test.ts
+++ b/server/test/unit/validation/monitorValidation.test.ts
@@ -278,6 +278,53 @@ describe("monitorValidation — HEAD method gating", () => {
 	});
 });
 
+describe("monitorValidation — regex pattern gating", () => {
+	const baseRegex = {
+		name: "regex check",
+		type: "http" as const,
+		url: "https://example.com",
+		useAdvancedMatching: true,
+		matchMethod: "regex" as const,
+	};
+
+	describe("createMonitorBodyValidation", () => {
+		it("accepts an RE2-supported regex pattern", () => {
+			const parsed = createMonitorBodyValidation.parse({ ...baseRegex, expectedValue: "^2\\d{2}$" });
+			expect(parsed.expectedValue).toBe("^2\\d{2}$");
+		});
+
+		it("rejects a pattern using a backreference", () => {
+			expect(() => createMonitorBodyValidation.parse({ ...baseRegex, expectedValue: "(a+)\\1" })).toThrow();
+		});
+
+		it("rejects a pattern using lookahead", () => {
+			expect(() => createMonitorBodyValidation.parse({ ...baseRegex, expectedValue: "foo(?=bar)" })).toThrow();
+		});
+
+		it("ignores an invalid regex when matchMethod is not 'regex'", () => {
+			const parsed = createMonitorBodyValidation.parse({ ...baseRegex, matchMethod: "include", expectedValue: "(a+)\\1" });
+			expect(parsed.expectedValue).toBe("(a+)\\1");
+		});
+
+		it("ignores an empty expectedValue", () => {
+			const parsed = createMonitorBodyValidation.parse({ ...baseRegex, expectedValue: "" });
+			expect(parsed.matchMethod).toBe("regex");
+		});
+	});
+
+	describe("editMonitorBodyValidation", () => {
+		it("rejects a pattern using a backreference", () => {
+			expect(() => editMonitorBodyValidation.parse({ matchMethod: "regex", expectedValue: "(a+)\\1" })).toThrow();
+		});
+	});
+
+	describe("importMonitorsBodyValidation", () => {
+		it("rejects a pattern using a backreference on imported monitors", () => {
+			expect(() => importMonitorsBodyValidation.parse({ monitors: [{ ...baseRegex, expectedValue: "(a+)\\1" }] })).toThrow();
+		});
+	});
+});
+
 describe("monitorValidation — customUpCodes", () => {
 	const baseHttpBody = {
 		name: "HTTP check",