diff --git a/src/core/anonymize-utils.ts b/src/core/anonymize-utils.ts
index 7a17e01..efc3065 100644
--- a/src/core/anonymize-utils.ts
+++ b/src/core/anonymize-utils.ts
@@ -292,11 +292,17 @@ function compileTerms(terms: string[] | undefined): CompiledTermVariant[] {
         unicode: variant.unicode,
       });
       const baseFlags = variant.unicode ? "iu" : "i";
-      compiled.push({
-        replaceRegex: new RegExp(bounded, "g" + baseFlags),
-        testRegex: new RegExp(bounded, baseFlags),
-        mask,
-      });
+      // A user-supplied regex can be valid without `u` but illegal with it
+      // (e.g. `[\w-\.]` — a range between class shorthands is rejected only
+      // in unicode mode). Skip variants that fail to compile so the other
+      // variant still anonymizes.
+      try {
+        const replaceRegex = new RegExp(bounded, "g" + baseFlags);
+        const testRegex = new RegExp(bounded, baseFlags);
+        compiled.push({ replaceRegex, testRegex, mask });
+      } catch {
+        continue;
+      }
     }
   }
   return compiled;
diff --git a/src/server/routes/route-utils.ts b/src/server/routes/route-utils.ts
index fa4a54c..06e3a79 100644
--- a/src/server/routes/route-utils.ts
+++ b/src/server/routes/route-utils.ts
@@ -114,12 +114,42 @@ export function isOwnerCoauthorOrAdmin(repo: Repository, user: User) {
   });
 }
 
+// Pull the first project-relevant frame ("file:line:col") out of a stack so
+// background-job errors (no req.originalUrl) still get a debug pointer in the
+// `url` slot. Skips node internals and node_modules.
+function originFromStack(stack: unknown): string | undefined {
+  if (typeof stack !== "string") return undefined;
+  const lines = stack.split("\n");
+  for (const line of lines) {
+    const m = line.match(/\(([^()\s]+:\d+:\d+)\)\s*$/) ||
+      line.match(/at\s+([^()\s]+:\d+:\d+)\s*$/);
+    if (!m) continue;
+    const loc = m[1];
+    if (loc.startsWith("node:") || loc.includes("node_modules")) continue;
+    return loc;
+  }
+  return undefined;
+}
+
+function ensureUrl(
+  payload: Record<string, unknown>,
+  req?: express.Request
+) {
+  if (req?.originalUrl) {
+    payload.url = req.originalUrl;
+    return;
+  }
+  if (typeof payload.url === "string" && payload.url) return;
+  const origin = originFromStack(payload.stack);
+  if (origin) payload.url = origin;
+}
+
 // eslint-disable-next-line @typescript-eslint/no-explicit-any
 function printError(error: any, req?: express.Request) {
   if (error instanceof AnonymousError) {
     if (req?.originalUrl === "/api/repo/undefined/options") return;
     const payload: Record<string, unknown> = serializeError(error);
-    if (req?.originalUrl) payload.url = req.originalUrl;
+    ensureUrl(payload, req);
     // Use the error's snake_case message as the logger summary so the admin
     // Errors page surfaces something meaningful (e.g. "repoId_already_used")
     // instead of a generic "anonymous error" wrapper.
@@ -135,7 +165,7 @@ function printError(error: any, req?: express.Request) {
     }
   } else if (error instanceof HTTPError) {
     const payload: Record<string, unknown> = serializeError(error);
-    if (req?.originalUrl) payload.url = req.originalUrl;
+    ensureUrl(payload, req);
     logger.error(error.code || error.name || "HTTPError", payload);
   } else {
     // Unhandled errors: use the error class name (SyntaxError, TypeError,
@@ -148,7 +178,7 @@ function printError(error: any, req?: express.Request) {
     ) {
       serialized.httpStatus = 500;
     }
-    if (req?.originalUrl) serialized.url = req.originalUrl;
+    ensureUrl(serialized, req);
     const summary =
       (error && typeof error === "object" &&
         ((error as { name?: string }).name ||
diff --git a/test/anonymize-utils.test.js b/test/anonymize-utils.test.js
index 469cd69..e195382 100644
--- a/test/anonymize-utils.test.js
+++ b/test/anonymize-utils.test.js
@@ -119,6 +119,12 @@ class ContentAnonimizer {
           unicode: variant.unicode,
         });
         const flags = variant.unicode ? "giu" : "gi";
+        let regex;
+        try {
+          regex = new RegExp(bounded, flags);
+        } catch {
+          continue;
+        }
         content = content.replace(urlRegex, (match) => {
           if (new RegExp(bounded, flags).test(match)) {
             this.wasAnonymized = true;
@@ -126,7 +132,7 @@ class ContentAnonimizer {
           }
           return match;
         });
-        content = content.replace(new RegExp(bounded, flags), () => {
+        content = content.replace(regex, () => {
           this.wasAnonymized = true;
           return mask;
         });
@@ -217,6 +223,21 @@ describe("ContentAnonimizer", function () {
       expect(() => anon.anonymize("some foo(bar here")).to.not.throw();
     });
 
+    // A user regex valid without `u` but illegal with it (range between
+    // class shorthands like `[\w-\.]`) must not crash compilation; the
+    // non-unicode variant should still anonymize matches.
+    it("accepts a regex that only compiles without the unicode flag", function () {
+      const anon = new ContentAnonimizer({
+        terms: ["[\\w-\\.]+@([\\w-]+\\.)+[\\w-]{2,4}"],
+      });
+      let result;
+      expect(() => {
+        result = anon.anonymize("contact me at alice@example.com please");
+      }).to.not.throw();
+      expect(result).to.not.include("alice@example.com");
+      expect(result).to.include("XXXX-1");
+    });
+
     // #175 — terms starting with a non-word char (e.g. "@username") were
     // silently skipped because \b can't match between two non-word chars.
     it("replaces terms starting with a non-word character (e.g. @user)", function () {