diff --git a/apps/desktop/src/lib/naming/namingStyleTransformers.ts b/apps/desktop/src/lib/naming/namingStyleTransformers.ts
index 7756d12a41..e834db97ec 100644
--- a/apps/desktop/src/lib/naming/namingStyleTransformers.ts
+++ b/apps/desktop/src/lib/naming/namingStyleTransformers.ts
@@ -10,11 +10,44 @@ export const SINGLE_IDENTIFIER_PATTERN = /^[A-Za-z0-9_$-]+$/;
 const LEADING_SEPARATOR_PATTERN = /^[_$-]+/;
 const TRAILING_SEPARATOR_PATTERN = /[_$-]+$/;
 const SEPARATOR_RUN_PATTERN = /[_$-]+/;
-// Word boundaries inside an identifier segment: lower→Upper (userName),
-// UPPER→Upper+lower (HTTPServer), and digit→letter (user2Name / sha256Hash).
-// Letter→digit is deliberately NOT a boundary so digit runs stay attached to
-// the preceding word (ipv4, sha256, field1).
-const WORD_BOUNDARY_PATTERN = /(?<=[a-z])(?=[A-Z])|(?<=[A-Z])(?=[A-Z][a-z])|(?<=[0-9])(?=[A-Za-z])/;
+
+function isLower(letter: string): boolean {
+  return letter >= "a" && letter <= "z";
+}
+
+function isUpper(letter: string): boolean {
+  return letter >= "A" && letter <= "Z";
+}
+
+function isDigit(letter: string): boolean {
+  return letter >= "0" && letter <= "9";
+}
+
+/**
+ * Split a separator-free segment on its internal word boundaries: lower→Upper
+ * (userName), UPPER→Upper+lower (HTTPServer), and digit→letter (user2Name /
+ * sha256Hash). Letter→digit is deliberately NOT a boundary so digit runs stay
+ * attached to the preceding word (ipv4, sha256, field1).
+ *
+ * Implemented as a character scan instead of a zero-width lookbehind regex
+ * because lookbehind throws at module-parse time on WebViews older than
+ * Safari 16.4 and crashed the whole app there (issue #8202 / #6521 class).
+ */
+function splitSegmentOnWordBoundaries(segment: string): string[] {
+  const words: string[] = [];
+  let start = 0;
+  for (let index = 1; index < segment.length; index++) {
+    const previous = segment[index - 1];
+    const current = segment[index];
+    const next = segment[index + 1];
+    const boundary = (isLower(previous) && isUpper(current)) || (isUpper(previous) && isUpper(current) && isLower(next)) || (isDigit(previous) && (isLower(current) || isUpper(current)));
+    if (!boundary) continue;
+    words.push(segment.slice(start, index));
+    start = index;
+  }
+  words.push(segment.slice(start));
+  return words;
+}
 
 interface IdentifierParts {
   leading: string;
@@ -30,7 +63,7 @@ function splitIntoWords(core: string): IdentifierParts {
   const inner = core.slice(leading.length, core.length - trailing.length);
   const words = inner
     .split(SEPARATOR_RUN_PATTERN)
-    .flatMap((segment) => segment.split(WORD_BOUNDARY_PATTERN))
+    .flatMap(splitSegmentOnWordBoundaries)
     .filter((word) => word.length > 0);
   return { leading, words, trailing };
 }
diff --git a/apps/desktop/src/lib/ui/__tests__/legacyWebViewRegexCompat.spec.ts b/apps/desktop/src/lib/ui/__tests__/legacyWebViewRegexCompat.spec.ts
new file mode 100644
index 0000000000..70b3bb83b9
--- /dev/null
+++ b/apps/desktop/src/lib/ui/__tests__/legacyWebViewRegexCompat.spec.ts
@@ -0,0 +1,50 @@
+import { readFileSync, readdirSync, statSync } from "node:fs";
+import { fileURLToPath } from "node:url";
+import path from "node:path";
+import { describe, expect, it } from "vitest";
+
+const SOURCE_EXTENSIONS = new Set([".ts", ".vue"]);
+// Workspace sources that ship in the WebView bundle. Named capture groups
+// (`(?<name>…)`) are fine — Safari 10.1+ supports them; lookbehind
+// (`(?<=…)` / `(?<!…)`) is not — old WebKit (< Safari 16.4, e.g. macOS 12)
+// throws "invalid group specifier name" while *parsing the module*, which
+// kills the whole app at startup (issues #6521 and #8202), so guard every
+// bundled source, not just the file that regressed last time.
+const BUNDLED_SOURCE_ROOTS = ["apps/desktop/src", "packages/mongo-shell/src"];
+
+function collectSourceFiles(directory: string, files: string[] = []): string[] {
+  for (const entry of readdirSync(directory)) {
+    if (entry === "__tests__" || entry.startsWith(".")) continue;
+    const fullPath = path.join(directory, entry);
+    if (statSync(fullPath).isDirectory()) {
+      collectSourceFiles(fullPath, files);
+    } else if (SOURCE_EXTENSIONS.has(path.extname(entry))) {
+      files.push(fullPath);
+    }
+  }
+  return files;
+}
+
+const workspaceRoot = path.resolve(fileURLToPath(import.meta.url), "../../../../../../..");
+const bundledSources = BUNDLED_SOURCE_ROOTS.flatMap((relativeRoot) => collectSourceFiles(path.join(workspaceRoot, relativeRoot)));
+
+// The runtime feature probe in legacyWebView.ts constructs its lookbehind
+// from a string inside try/catch (module still parses on old WebKit; the
+// engine that throws is the one being detected), so it is the sole allowed
+// exception.
+const LOOKBEHIND_ALLOWLIST = new Set(["apps/desktop/src/lib/ui/legacyWebView.ts"]);
+
+describe("WebView startup sources stay compatible with old WebKit regex syntax", () => {
+  it("ships no lookbehind assertions in bundled sources", () => {
+    expect(bundledSources.length).toBeGreaterThan(1000);
+
+    const offenders = bundledSources
+      .filter((file) => {
+        const source = readFileSync(file, "utf8");
+        return source.includes("(?<=") || source.includes("(?<!");
+      })
+      .map((file) => path.relative(workspaceRoot, file))
+      .filter((relative) => !LOOKBEHIND_ALLOWLIST.has(relative));
+    expect(offenders).toEqual([]);
+  });
+});
diff --git a/apps/desktop/src/lib/ui/legacyWebView.ts b/apps/desktop/src/lib/ui/legacyWebView.ts
index 7527588019..dcb3f4bc88 100644
--- a/apps/desktop/src/lib/ui/legacyWebView.ts
+++ b/apps/desktop/src/lib/ui/legacyWebView.ts
@@ -48,9 +48,15 @@ export function missingLegacyWebViewCapabilities(): string[] {
  * expressions with lookbehind or the named-group shapes Shiki's JavaScript
  * engine generates from TextMate grammars. Callers use this to pick a regex
  * engine (e.g. Shiki's Oniguruma WASM engine) that old WebKit can run.
+ *
+ * The pattern below is the only permitted lookbehind in bundled sources: it
+ * is constructed inside a try/catch at call time (not at module parse time),
+ * so the engine that cannot compile it is exactly the one being detected.
+ * legacyWebViewRegexCompat.spec.ts allows this file by name.
  */
 export function supportsRegExpLookbehind(): boolean {
   try {
+    // Probe compiled from a string so this module still parses on old WebKit.
     new RegExp("(?<=a)b");
     return true;
   } catch {