diff --git a/src/utils/envUtils.test.ts b/src/utils/envUtils.test.ts
new file mode 100644
index 000000000..d3e4a94f8
--- /dev/null
+++ b/src/utils/envUtils.test.ts
@@ -0,0 +1,99 @@
+import { afterEach, beforeEach, describe, expect, test } from 'bun:test'
+import { hasNodeOption } from './envUtils.js'
+
+describe('hasNodeOption', () => {
+  const originalNodeOptions = process.env.NODE_OPTIONS
+
+  afterEach(() => {
+    if (originalNodeOptions === undefined) {
+      delete process.env.NODE_OPTIONS
+    } else {
+      process.env.NODE_OPTIONS = originalNodeOptions
+    }
+  })
+
+  beforeEach(() => {
+    delete process.env.NODE_OPTIONS
+  })
+
+  // Table-driven regression coverage requested in PR #2188 review:
+  // - exact and equals positives for both CA flags
+  // - double-quoted positives
+  // - literal single-quoted negatives (Node keeps single quotes literal)
+  // - repeated whitespace / empty tokens
+  // - --inspect vs --inspect-brk boundary
+  // Each row restores NODE_OPTIONS after the case via afterEach.
+  const cases: Array<{
+    name: string
+    nodeOptions: string | undefined
+    flag: string
+    expected: boolean
+  }> = [
+    // Undefined / empty
+    { name: 'undefined NODE_OPTIONS returns false', nodeOptions: undefined, flag: '--use-system-ca', expected: false },
+    { name: 'empty string returns false', nodeOptions: '', flag: '--use-system-ca', expected: false },
+    { name: 'whitespace only returns false', nodeOptions: '   \t  ', flag: '--use-system-ca', expected: false },
+
+    // --use-system-ca exact / equals
+    { name: '--use-system-ca exact match', nodeOptions: '--use-system-ca', flag: '--use-system-ca', expected: true },
+    { name: '--use-system-ca with =value', nodeOptions: '--use-system-ca=1', flag: '--use-system-ca', expected: true },
+    { name: '--use-system-ca double-quoted exact', nodeOptions: '"--use-system-ca"', flag: '--use-system-ca', expected: true },
+    { name: '--use-system-ca double-quoted with =value', nodeOptions: '"--use-system-ca=1"', flag: '--use-system-ca', expected: true },
+    { name: "--use-system-ca single-quoted is literal (negative)", nodeOptions: "'--use-system-ca'", flag: '--use-system-ca', expected: false },
+    { name: "--use-system-ca single-quoted with =value is literal (negative)", nodeOptions: "'--use-system-ca=1'", flag: '--use-system-ca', expected: false },
+
+    // --use-openssl-ca exact / equals
+    { name: '--use-openssl-ca exact match', nodeOptions: '--use-openssl-ca', flag: '--use-openssl-ca', expected: true },
+    { name: '--use-openssl-ca with =value', nodeOptions: '--use-openssl-ca=1', flag: '--use-openssl-ca', expected: true },
+    { name: '--use-openssl-ca double-quoted exact', nodeOptions: '"--use-openssl-ca"', flag: '--use-openssl-ca', expected: true },
+    { name: "--use-openssl-ca single-quoted is literal (negative)", nodeOptions: "'--use-openssl-ca'", flag: '--use-openssl-ca', expected: false },
+
+    // Repeated whitespace / multiple tokens
+    { name: 'repeated whitespace between flags', nodeOptions: '  --use-system-ca   --use-openssl-ca  ', flag: '--use-system-ca', expected: true },
+    { name: 'repeated whitespace second flag', nodeOptions: '  --use-system-ca   --use-openssl-ca  ', flag: '--use-openssl-ca', expected: true },
+    { name: 'multiple spaces and tabs', nodeOptions: '--use-system-ca\t  --max-old-space-size=4096', flag: '--max-old-space-size', expected: true },
+    { name: 'flag not present with repeated whitespace', nodeOptions: '  --use-system-ca   ', flag: '--use-openssl-ca', expected: false },
+
+    // --inspect vs --inspect-brk boundary
+    { name: '--inspect exact', nodeOptions: '--inspect', flag: '--inspect', expected: true },
+    { name: '--inspect with =value', nodeOptions: '--inspect=0.0.0.0:9229', flag: '--inspect', expected: true },
+    { name: '--inspect double-quoted with =value', nodeOptions: '"--inspect=0.0.0.0:9229"', flag: '--inspect', expected: true },
+    { name: '--inspect-brk does not match --inspect (prefix without =)', nodeOptions: '--inspect-brk=9229', flag: '--inspect', expected: false },
+    { name: '--inspect-brk exact matches itself', nodeOptions: '--inspect-brk=9229', flag: '--inspect-brk', expected: true },
+    { name: '--inspect-brk exact', nodeOptions: '--inspect-brk', flag: '--inspect-brk', expected: true },
+    { name: '--inspect does not match --inspect-brk', nodeOptions: '--inspect', flag: '--inspect-brk', expected: false },
+    { name: '--inspect single-quoted is literal (negative)', nodeOptions: "'--inspect'", flag: '--inspect', expected: false },
+    { name: '--inspect-brk single-quoted is literal (negative for --inspect)', nodeOptions: "'--inspect-brk=9229'", flag: '--inspect', expected: false },
+
+    // --max-old-space-size (original PR motivation)
+    { name: '--max-old-space-size with =value', nodeOptions: '--max-old-space-size=4096', flag: '--max-old-space-size', expected: true },
+    { name: '--max-old-space-size double-quoted with =value', nodeOptions: '"--max-old-space-size=4096"', flag: '--max-old-space-size', expected: true },
+    { name: "--max-old-space-size single-quoted is literal (negative)", nodeOptions: "'--max-old-space-size=4096'", flag: '--max-old-space-size', expected: false },
+    { name: '--max-old-space-size exact without value', nodeOptions: '--max-old-space-size', flag: '--max-old-space-size', expected: true },
+    { name: '--max-old-space-size not confused with prefix', nodeOptions: '--max-old-space-size-extra', flag: '--max-old-space-size', expected: false },
+
+    // Mixed flags
+    { name: 'mixed flags contains target', nodeOptions: '--experimental-vm-modules --max-old-space-size=4096 --inspect=9229', flag: '--max-old-space-size', expected: true },
+    { name: 'mixed flags does not contain absent', nodeOptions: '--experimental-vm-modules --max-old-space-size=4096', flag: '--use-system-ca', expected: false },
+  ]
+
+  for (const { name, nodeOptions, flag, expected } of cases) {
+    test(name, () => {
+      if (nodeOptions === undefined) {
+        delete process.env.NODE_OPTIONS
+      } else {
+        process.env.NODE_OPTIONS = nodeOptions
+      }
+      expect(hasNodeOption(flag)).toBe(expected)
+    })
+  }
+
+  test('does not leak NODE_OPTIONS between cases (sanity)', () => {
+    // This test runs after the table; afterEach should have restored original.
+    // Set a distinct value and verify it does not persist to next test via afterEach,
+    // but here we just verify the helper reads current env.
+    process.env.NODE_OPTIONS = '--use-system-ca'
+    expect(hasNodeOption('--use-system-ca')).toBe(true)
+    expect(hasNodeOption('--use-openssl-ca')).toBe(false)
+  })
+})
diff --git a/src/utils/envUtils.ts b/src/utils/envUtils.ts
index f5b38a8de..f51186160 100644
--- a/src/utils/envUtils.ts
+++ b/src/utils/envUtils.ts
@@ -94,10 +94,13 @@ export function getProjectsDir(): string {
 
 /**
  * Check if NODE_OPTIONS contains a specific flag.
+ *
  * Handles `--flag=value` forms (e.g. `--max-old-space-size=4096`,
- * `--inspect=0.0.0.0:9229`) and quoted tokens. Matches exact flag
- * or flag with an `=value` suffix to avoid false positives on
- * prefix-related flags (e.g. `--inspect` must not match `--inspect-brk`).
+ * `--inspect=0.0.0.0:9229`) and double-quoted tokens (matching Node's
+ * option lexer; single quotes are literal once inside `process.env`).
+ * Matches exact flag or flag with an `=value` suffix to avoid false
+ * positives on prefix-related flags (e.g. `--inspect` must not match
+ * `--inspect-brk`).
  */
 export function hasNodeOption(flag: string): boolean {
   const nodeOptions = process.env.NODE_OPTIONS
@@ -106,10 +109,12 @@ export function hasNodeOption(flag: string): boolean {
   }
   const tokens = nodeOptions.split(/\s+/).filter(Boolean)
   for (let token of tokens) {
-    // Strip surrounding single/double quotes (NODE_OPTIONS may be quoted)
+    // Only double quotes are interpreted by Node's NODE_OPTIONS parser;
+    // single quotes are kept literal (Node leaves them as part of the token).
     if (
-      (token.startsWith('"') && token.endsWith('"')) ||
-      (token.startsWith("'") && token.endsWith("'"))
+      token.length >= 2 &&
+      token.startsWith('"') &&
+      token.endsWith('"')
     ) {
       token = token.slice(1, -1)
     }