diff --git a/.changeset/21125-oclif-core-5.md b/.changeset/21125-oclif-core-5.md
new file mode 100644
index 00000000000..040861cd6bf
--- /dev/null
+++ b/.changeset/21125-oclif-core-5.md
@@ -0,0 +1,9 @@
+---
+'@objectstack/cli': patch
+---
+
+`@objectstack/cli` moves to the `@oclif/core` 5 line: its `@oclif/core` dependency goes from `^4.13.3` to `^5.1.2`. The Command classes the package exports (`CompileCommand`, `ValidateCommand`, `ServeCommand` and the rest) now build on `@oclif/core` 5, so code that extends one of them or runs it beside its own oclif setup should use `@oclif/core` 5 as well.
+
+Node.js 22 or later is required. Every `@oclif/core` 5 release declares `engines.node` `>=22.0.0`, the same floor this package already declared.
+
+The `os` commands, flags and output are unchanged. On 5.1.2 every help page renders byte-for-byte as it did on 4.13.3. The published entry also answers `--version`, `--help`, an unknown command, an unknown flag and a refused `--port` with the same exit codes and the same bytes.
diff --git a/packages/cli/bin/run-dev.js b/packages/cli/bin/run-dev.js
index d01f74fd314..7388efd02d4 100644
--- a/packages/cli/bin/run-dev.js
+++ b/packages/cli/bin/run-dev.js
@@ -5,7 +5,7 @@
 // having been built. Not published (`files` does not name `bin/`, and only the
 // `bin` target itself is packed automatically).
 //
-// The body is `execute({ development: true })` from @oclif/core 4.13.3 inlined,
+// The body is `execute({ development: true })` from @oclif/core 5.1.2 inlined,
 // for the reason `bin/run.js` states: `execute` hands the error straight to
 // `handle()`, which prints a usage dump, and #10111 needs one unmistakable line
 // to land on stderr before it. `NODE_ENV` and `settings.debug` are what
diff --git a/packages/cli/bin/run.js b/packages/cli/bin/run.js
index 4e24ceca831..c400f736379 100755
--- a/packages/cli/bin/run.js
+++ b/packages/cli/bin/run.js
@@ -5,7 +5,7 @@
 // `files` never names the directory — see scripts/check-published-files.mjs).
 //
 // It used to be `await execute({ type: 'esm', dir: import.meta.url })`. What is
-// inlined below IS `execute()` from @oclif/core 4.13.3, verbatim apart from the
+// inlined below IS `execute()` from @oclif/core 5.1.2, verbatim apart from the
 // added lines, because `execute` swallows the error into `handle()` and
 // there is no hook between the two. `handle()` writes the parse error and then
 // a full usage dump; #10111 needs one unmistakable line to reach stderr FIRST,
@@ -31,7 +31,7 @@ import { flush, handle, run, settings } from '@oclif/core';
  * `development`/`test`, with no baseline and only two declared exceptions.
  *
  * What was missing is that **this file never asserted it about itself.**
- * `@oclif/core@4.13.3`'s `lib/config/ts-path.js` skips its TypeScript path
+ * `@oclif/core@5.1.2`'s `lib/config/ts-path.js` skips its TypeScript path
  * lookup only when `isProd()`, which `lib/util/util.js` defines as
  * `['development', 'test'].includes(process.env.NODE_ENV ?? '')` negated. So an
  * ambient `NODE_ENV` — exported by a developer, or inherited by any child this
diff --git a/packages/cli/package.json b/packages/cli/package.json
index c1b0c4b530a..9d84cdcf337 100644
--- a/packages/cli/package.json
+++ b/packages/cli/package.json
@@ -108,7 +108,7 @@
     "@objectstack/trigger-schedule": "workspace:*",
     "@objectstack/types": "workspace:*",
     "@objectstack/verify": "workspace:*",
-    "@oclif/core": "^4.13.3",
+    "@oclif/core": "^5.1.2",
     "bundle-require": "^5.1.0",
     "chalk": "^6.0.1",
     "chokidar": "^5.0.0",
@@ -137,8 +137,8 @@
     "@objectstack/connector-rest": "workspace:*",
     "@objectstack/driver-turso": "workspace:*",
     "@objectstack/plugin-dev": "workspace:*",
-    "@oclif/plugin-help": "^6.2.58",
-    "@oclif/plugin-plugins": "^5.4.87",
+    "@oclif/plugin-help": "^7.0.2",
+    "@oclif/plugin-plugins": "^7.0.3",
     "@types/better-sqlite3": "^7.6.13",
     "@types/node": "^26.6.3",
     "typescript": "^6.0.3",
diff --git a/packages/cli/src/utils/port-contract.ts b/packages/cli/src/utils/port-contract.ts
index 62a167b1708..6beee874007 100644
--- a/packages/cli/src/utils/port-contract.ts
+++ b/packages/cli/src/utils/port-contract.ts
@@ -35,7 +35,7 @@
  * ## ⚠️ Why the doors call this module EXPLICITLY, before spawning
  *
  * Not from an oclif flag `parse`, and not from `Flags.integer({ min, max })`.
- * MEASURED against this checkout's `@oclif/core` 4.13.3 — see
+ * MEASURED against this checkout's `@oclif/core` 5.1.2 — see
  * {@link describePortSource} for the runtime probe and its numbers — a flag's
  * `parse` never runs over that flag's `default`, and `Flags.integer`'s
  * `min`/`max` never runs over one either. `serve` reads `$OS_PORT`/`$PORT`
@@ -95,13 +95,13 @@ export type PortInputSource = '--port' | 'OS_PORT' | 'PORT' | 'the built-in defa
  * signal that separates `--port` from the environment here, because
  * `PORT`/`OS_PORT` never reach flag parsing at all — they are read by the
  * `default` expression on the flag. MEASURED against this checkout's
- * `@oclif/core` (4.13.3), both in `lib/parser/parse.js` and at runtime: the
+ * `@oclif/core` (5.1.2), both in `lib/parser/parse.js` and at runtime: the
  * default branch's value function is `async () => flag.default`, and unlike
  * the argv and `flag.env` branches it never calls `parseFlagOrThrowError`. A
  * flag's own `parse` therefore cannot see a default, which is exactly why the
  * validation this function feeds lives at the consumer instead of on the flag.
  *
- * ⚠️ RE-MEASURED for #12673 against the same `@oclif/core` 4.13.3, by driving
+ * ⚠️ RE-MEASURED for #12673 against the same `@oclif/core` 5.1.2, by driving
  * `Parser.parse` directly. Two results, and the second closes off the cheap
  * repair the issue asked about:
  *
@@ -372,7 +372,7 @@ export function strictPortReading(raw: string): number | null {
  * that fails silently when a future author forgets to pass it.
  *
  * `os start` normalises before forwarding — its `--port` is a `Flags.integer`
- * (parser `/^-?\d+$/` in `@oclif/core` 4.13.3), so the child receives
+ * (parser `/^-?\d+$/` in `@oclif/core` 5.1.2), so the child receives
  * `PORT=8080` for an `--port 08080`, and a spelling this notice fires on can
  * only reach it through the environment, under its own name.
  *
diff --git a/packages/cli/test/published-entry-node-env-source-reroute.test.ts b/packages/cli/test/published-entry-node-env-source-reroute.test.ts
index f99d5708269..88fdc609d02 100644
--- a/packages/cli/test/published-entry-node-env-source-reroute.test.ts
+++ b/packages/cli/test/published-entry-node-env-source-reroute.test.ts
@@ -6,7 +6,7 @@
  *
  * ## The defect
  *
- * `@oclif/core@4.13.3`'s `lib/config/ts-path.js` skips its TypeScript path
+ * `@oclif/core@5.1.2`'s `lib/config/ts-path.js` skips its TypeScript path
  * lookup only when `isProd()`, which `lib/util/util.js` defines as a negated
  * `['development', 'test'].includes(process.env.NODE_ENV ?? '')`. So an ambient
  * `NODE_ENV=development` — exported by a developer, or inherited by any child
diff --git a/packages/cli/test/serve-mcp-capability-collision.e2e.test.ts b/packages/cli/test/serve-mcp-capability-collision.e2e.test.ts
index fd9a75c0419..3314b060ed6 100644
--- a/packages/cli/test/serve-mcp-capability-collision.e2e.test.ts
+++ b/packages/cli/test/serve-mcp-capability-collision.e2e.test.ts
@@ -63,7 +63,7 @@ const HERE = resolve(fileURLToPath(import.meta.url), '..');
  * genuinely reaches it (#11707).
  *
  * Both halves of that are load-bearing and neither works alone. @oclif/core
- * 4.13.3 skips its TypeScript path lookup only when `isProd()` —
+ * 5.1.2 skips its TypeScript path lookup only when `isProd()` —
  * `!['development', 'test'].includes(process.env.NODE_ENV ?? '')` — so under a
  * child `NODE_ENV` of `development` or `test` it rewrites the command target
  * from the declared `./dist/commands` to `./src/commands` and transpiles, and
diff --git a/packages/cli/test/serve-mcp-stdio-answers.e2e.test.ts b/packages/cli/test/serve-mcp-stdio-answers.e2e.test.ts
index 973e1a7fe4d..cc0d3e60934 100644
--- a/packages/cli/test/serve-mcp-stdio-answers.e2e.test.ts
+++ b/packages/cli/test/serve-mcp-stdio-answers.e2e.test.ts
@@ -62,7 +62,7 @@ const HERE = resolve(fileURLToPath(import.meta.url), '..');
  * genuinely reaches it (#11707).
  *
  * Both halves of that are load-bearing and neither works alone. @oclif/core
- * 4.13.3 skips its TypeScript path lookup only when `isProd()` —
+ * 5.1.2 skips its TypeScript path lookup only when `isProd()` —
  * `!['development', 'test'].includes(process.env.NODE_ENV ?? '')` — so under a
  * child `NODE_ENV` of `development` or `test` it rewrites the command target
  * from the declared `./dist/commands` to `./src/commands` and transpiles, and
diff --git a/packages/cli/test/serve-stdio-stdout-purity.e2e.test.ts b/packages/cli/test/serve-stdio-stdout-purity.e2e.test.ts
index 650462c082e..68af611e933 100644
--- a/packages/cli/test/serve-stdio-stdout-purity.e2e.test.ts
+++ b/packages/cli/test/serve-stdio-stdout-purity.e2e.test.ts
@@ -59,7 +59,7 @@ const HERE = resolve(fileURLToPath(import.meta.url), '..');
  * genuinely reaches it (#11707).
  *
  * Both halves of that are load-bearing and neither works alone. @oclif/core
- * 4.13.3 skips its TypeScript path lookup only when `isProd()` —
+ * 5.1.2 skips its TypeScript path lookup only when `isProd()` —
  * `!['development', 'test'].includes(process.env.NODE_ENV ?? '')` — so under a
  * child `NODE_ENV` of `development` or `test` it rewrites the command target
  * from the declared `./dist/commands` to `./src/commands` and transpiles, and
diff --git a/packages/cli/test/unbuilt-workspace-lead.test.ts b/packages/cli/test/unbuilt-workspace-lead.test.ts
index 2cb8bcc351b..3022b6d711f 100644
--- a/packages/cli/test/unbuilt-workspace-lead.test.ts
+++ b/packages/cli/test/unbuilt-workspace-lead.test.ts
@@ -25,6 +25,12 @@
  * `isInvocationError` requires both) answers `undefined` for this failure and
  * why it could not be the place this lands.
  *
+ * Each fixture's `module:` line names the `@oclif/core` its run loaded
+ * (4.13.3) and stays as recorded, because a transcript is evidence of one run.
+ * Nothing here reads that line — the classifier works off `message:` — and
+ * `@oclif/core` 5.1.2 builds the detail from the same lines in the same order,
+ * re-measured when the CLI moved to the 5 line.
+ *
  * ⚠️ This file pins the decision only. Whether `bin/run-dev.js` actually asks
  * the question and prints the answer is a different fact with its own test —
  * `run-dev-unbuilt-workspace.e2e.test.ts` drives the real binary, and deleting
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 30ba2147a56..2957d82b79c 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -590,8 +590,8 @@ importers:
         specifier: workspace:*
         version: link:../verify
       '@oclif/core':
-        specifier: ^4.13.3
-        version: 4.13.3
+        specifier: ^5.1.2
+        version: 5.1.2
       bundle-require:
         specifier: ^5.1.0
         version: 5.1.0(esbuild@0.28.2)
@@ -639,11 +639,11 @@ importers:
         specifier: workspace:*
         version: link:../plugins/plugin-dev
       '@oclif/plugin-help':
-        specifier: ^6.2.58
-        version: 6.2.58
+        specifier: ^7.0.2
+        version: 7.0.2
       '@oclif/plugin-plugins':
-        specifier: ^5.4.87
-        version: 5.4.87
+        specifier: ^7.0.3
+        version: 7.0.3
       '@types/better-sqlite3':
         specifier: ^7.6.13
         version: 7.6.13
@@ -4329,17 +4329,17 @@ packages:
   '@nodable/entities@3.0.0':
     resolution: {integrity: sha512-8L9xFeTYKhm49xfIypoe2W5wV1m/3Z58kT+7kR9A8OyFxcPduI4VmxaUMQyKYrRjUoLLSXv6EKKID5Tvj9cUVw==}
 
-  '@oclif/core@4.13.3':
-    resolution: {integrity: sha512-wBp2igI2KVwq2ZmpnfmGtOROo7aXZIr3OEtAS16g1wHFBqyEuswL+9K50NJWJvlpAmxd+4dVj/ycawXESU3wQQ==}
-    engines: {node: '>=18.0.0'}
+  '@oclif/core@5.1.2':
+    resolution: {integrity: sha512-vgbWWFKjjsf7oAbJONFPnDkVNeqmy70DTBUjsprW/HRiTrXe8sMlFc0ih8GjpU+dn+m6V2ksaZjBV9HgnsmWVg==}
+    engines: {node: '>=22.0.0'}
 
-  '@oclif/plugin-help@6.2.58':
-    resolution: {integrity: sha512-DAYMXZrTWRMLTbpX+rT+ibAmKrZ6IVNGn+fgAGjMoeNlqlSY94eJHocgmqChMwsdWp3H3x+jFmPJiYQt/ifr3Q==}
-    engines: {node: '>=18.0.0'}
+  '@oclif/plugin-help@7.0.2':
+    resolution: {integrity: sha512-xqYsSECa7HrO+yb20ukcRzlz86Tq6f7Ft48kp4YLka0/4X5WbehOCSLdKlV8ejdcfK5gQzC4erMNeIXxyF5aXQ==}
+    engines: {node: '>=22.0.0'}
 
-  '@oclif/plugin-plugins@5.4.87':
-    resolution: {integrity: sha512-ym2/26p7J9O5POKjHOysJLSNcpWZK5mxzY3gwFYBaSgQRsjFRBdkZ8d7NcHOuES/E4ZnoP5Q3iNu+v4uhvNTDw==}
-    engines: {node: '>=18.0.0'}
+  '@oclif/plugin-plugins@7.0.3':
+    resolution: {integrity: sha512-ufjwLdKbw5AC8BjguvRGRBFoSc8RGXV1TVjxMDr8smJuN8QM4yhZIvKCoSVQC24BX71pF75LrvQEWpwQJbwpQA==}
+    engines: {node: '>=22.0.0'}
 
   '@open-draft/deferred-promise@2.2.0':
     resolution: {integrity: sha512-CecwLWx3rhxVQF6V4bAgPS5t+So2sTbPgAzafKkVizyi7tlwpcFpdFqq+wqF2OwNBmqFuu6tOyouTuxgpMfzmA==}
@@ -6413,9 +6413,9 @@ packages:
   ee-first@1.1.1:
     resolution: {integrity: sha512-WMwm9LhRUo+WUaRN+vRuETqG89IgZphVSNkdFgeb6sS/E4OrDIN7t48CAewSHXc6C8lefD8KKfr5vY61brQlow==}
 
-  ejs@3.1.10:
-    resolution: {integrity: sha512-UeJmFfOrAQS8OJWPZ4qtgHyWExa088/MtK5UEyoJGFH67cDEXkZSviOiKRCZ4Xij0zxI3JECgYs3oKx+AizQBA==}
-    engines: {node: '>=0.10.0'}
+  ejs@6.0.1:
+    resolution: {integrity: sha512-UaaM14yby8U3k02ihS1Bmj5Kz2d7CCQM1scxpgs4Mhkq8F1wR2gl3+Ts4h5Ne4Mnt7M9m4Dw7jsuMr3+xO4vZA==}
+    engines: {node: '>=0.12.18'}
     hasBin: true
 
   emoji-regex@8.0.0:
@@ -6684,9 +6684,6 @@ packages:
   file-uri-to-path@1.0.0:
     resolution: {integrity: sha512-0Zt+s3L7Vf1biwWZ29aARiVYLx7iMGnEUl9x33fbB/j3jR81u/O2LbqK+Bm1CDSNDKVtJ/YjwY7TUd5SkeLQLw==}
 
-  filelist@1.0.6:
-    resolution: {integrity: sha512-5giy2PkLYY1cP39p17Ech+2xlpTRL9HLspOfEgm0L6CwBXBTgsK5ou0JtzYuepxkaQ/tvhCFIJ5uXo0OrM2DxA==}
-
   finalhandler@2.1.1:
     resolution: {integrity: sha512-S8KoZgRZN+a5rNwqTxlZZePjT/4cnm0ROV70LedRHZ0p8u9fRID0hJUZQpkKLzro8LfmC8sx23bY6tVNxv8pQA==}
     engines: {node: '>= 18.0.0'}
@@ -7108,11 +7105,6 @@ packages:
   is-decimal@2.0.1:
     resolution: {integrity: sha512-AAB9hiomQs5DXWcRB1rqsxGUstbRroFOPPVAomNk/3XHR5JyEZChOyTWe2oayKnsSsr/kcGqF+z6yuH6HHpN0A==}
 
-  is-docker@2.2.1:
-    resolution: {integrity: sha512-F+i2BKsFrH66iaUFc0woD8sLy8getkwTwtOBjvs56Cx4CgJDeKQeqfz8wAYiSb8JOprWhHH5p77PbmYCvvUuXQ==}
-    engines: {node: '>=8'}
-    hasBin: true
-
   is-docker@3.0.0:
     resolution: {integrity: sha512-eljcgEDlEns/7AXFosB5K/2nCM4P7FQPkGc/DWLy5rmFEWvZayGrik1d9/QIY5nJ4f9YsVvBkA6kJpHn9rISdQ==}
     engines: {node: ^12.20.0 || ^14.13.1 || >=16.0.0}
@@ -7160,10 +7152,6 @@ packages:
   is-unsafe@2.0.0:
     resolution: {integrity: sha512-2LdV822R+wmI86unXA93WCFpL6g+av8ynWk0nrHyJqGop5VoocYsSLFgN8jrfalT6iGeLNM4KXuVSsULP53kEA==}
 
-  is-wsl@2.2.0:
-    resolution: {integrity: sha512-fKzAra0rGJUUBwGBgNkHZuToZcn+TtXHpeCgmkMJMMYx1sQDYaCSyjJBSCa2nH1DGm7s3n1oBnohoVTBaN7Lww==}
-    engines: {node: '>=8'}
-
   is-wsl@3.1.1:
     resolution: {integrity: sha512-e6rvdUCiQCAuumZslxRJWR/Doq4VpPR82kqclvcS0efgt430SlGIk05vdCN58+VrzgtIcfNODjozVielycD4Sw==}
     engines: {node: '>=16'}
@@ -7194,11 +7182,6 @@ packages:
     resolution: {integrity: sha512-HGYWWS/ehqTV3xN10i23tkPkpH46MLCIMFNCaaKNavAXTF1RkqxawEPtnjnGZ6XKSInBKkiOA5BKS+aZiY3AvA==}
     engines: {node: '>=8'}
 
-  jake@10.9.4:
-    resolution: {integrity: sha512-wpHYzhxiVQL+IV05BLE2Xn34zW1S223hvjtqk0+gsPrwd/8JNLXJgZZM/iPFsYc1xyphF+6M6EvdE5E9MBGkDA==}
-    engines: {node: '>=10'}
-    hasBin: true
-
   jiti@2.7.0:
     resolution: {integrity: sha512-AC/7JofJvZGrrneWNaEnJeOLUx+JlGt7tNa0wZiRPT4MY1wmfKjt2+6O2p2uz2+skll8OZZmJMNqeke7kKbNgQ==}
     hasBin: true
@@ -8060,8 +8043,8 @@ packages:
     resolution: {integrity: sha512-K1HmQeZT2HrjpsR6KgqbN2FAXL2NrJJmNUSD9ck7HGTVu1JKXox8n9SB+tjbU8m8JGLF4OscrroPepew/L7/Xw==}
     engines: {node: ^12.22.0 || ^14.17.0 || >=16.0.0}
 
-  npm@11.19.0:
-    resolution: {integrity: sha512-SDd/hHg3KqHE5Ht2NHWxNYNtqCQ2pXAPLl6OtQhPyED5PHsRfrOtO199MZTIG2cQoQ1ZRI9t28shrD+2cr3AAw==}
+  npm@11.21.0:
+    resolution: {integrity: sha512-Zov8KhamNneiLdELtj5YALtNmJW4L4fCLTzjfpzXG2w6MSHcf0UxgdlK5uloCuksWT+7mGUU7wi79cO6RqivPg==}
     engines: {node: ^20.17.0 || >=22.9.0}
     hasBin: true
     bundledDependencies:
@@ -8384,6 +8367,10 @@ packages:
     resolution: {integrity: sha512-9ZhXKM/rw350N1ovuWHbGxnGh/SNJ4cnxHiM0rxE4VN41wsg8P8zWn9hv/buK00RP4WvlOyr/RBDiptyxVbkZQ==}
     engines: {node: '>=0.10.0'}
 
+  powershell-utils@0.1.0:
+    resolution: {integrity: sha512-dM0jVuXJPsDN6DvRpea484tCUaMiXWjuCn++HGTqUWzGDjv5tZkEZldAJ/UMlqRYGFrD/etByo4/xOuC/snX2A==}
+    engines: {node: '>=20'}
+
   prebuild-install@7.1.3:
     resolution: {integrity: sha512-8Mf2cbV7x1cXPUILADGI3wuhfqWvtiLA1iclTDbFRZkgRQS0NqsPZphna9V+HyTEadheuPmjaJMsbzKQFOzLug==}
     engines: {node: '>=10'}
@@ -9348,6 +9335,10 @@ packages:
     resolution: {integrity: sha512-h3Fbisa2nKGPxCpm89Hk33lBLsnaGBvctQopaBSOW/uIs6FTe1ATyAnKFJrzVs9vpGdsTe73WF3V4lIsk4Gacw==}
     engines: {node: '>=18'}
 
+  wsl-utils@0.4.0:
+    resolution: {integrity: sha512-9YmF+2sFEd+T7TkwlmE337F0IVzfDvDknhtpBQxxXzEOfgPphGlFYpyx0cTuCIFj8/p+sqwBYAeGxOMNSzPPDA==}
+    engines: {node: '>=20'}
+
   xml-crypto@6.1.2:
     resolution: {integrity: sha512-leBOVQdVi8FvPJrMYoum7Ici9qyxfE4kVi+AkpUoYCSXaQF4IlBm1cneTK9oAxR61LpYxTx7lNcsnBIeRpGW2w==}
     engines: {node: '>=16'}
@@ -10761,17 +10752,16 @@ snapshots:
 
   '@nodable/entities@3.0.0': {}
 
-  '@oclif/core@4.13.3':
+  '@oclif/core@5.1.2':
     dependencies:
       ansi-escapes: 4.3.2
       ansis: 3.17.0
       clean-stack: 3.0.1
       cli-spinners: 2.9.2
       debug: 4.4.3(supports-color@8.1.1)
-      ejs: 3.1.10
+      ejs: 6.0.1
       get-package-type: 0.1.0
       indent-string: 4.0.0
-      is-wsl: 2.2.0
       lilconfig: 3.1.3
       minimatch: 10.2.6
       semver: 7.8.5
@@ -10781,17 +10771,18 @@ snapshots:
       widest-line: 3.1.0
       wordwrap: 1.0.0
       wrap-ansi: 7.0.0
+      wsl-utils: 0.4.0
 
-  '@oclif/plugin-help@6.2.58':
+  '@oclif/plugin-help@7.0.2':
     dependencies:
-      '@oclif/core': 4.13.3
+      '@oclif/core': 5.1.2
 
-  '@oclif/plugin-plugins@5.4.87':
+  '@oclif/plugin-plugins@7.0.3':
     dependencies:
-      '@oclif/core': 4.13.3
+      '@oclif/core': 5.1.2
       ansis: 3.17.0
       debug: 4.4.3(supports-color@8.1.1)
-      npm: 11.19.0
+      npm: 11.21.0
       npm-package-arg: 11.0.3
       npm-run-path: 5.3.0
       object-treeify: 4.0.1
@@ -12728,9 +12719,7 @@ snapshots:
 
   ee-first@1.1.1: {}
 
-  ejs@3.1.10:
-    dependencies:
-      jake: 10.9.4
+  ejs@6.0.1: {}
 
   emoji-regex@8.0.0: {}
 
@@ -13099,10 +13088,6 @@ snapshots:
   file-uri-to-path@1.0.0:
     optional: true
 
-  filelist@1.0.6:
-    dependencies:
-      minimatch: 10.2.6
-
   finalhandler@2.1.1:
     dependencies:
       debug: 4.4.3(supports-color@8.1.1)
@@ -13605,8 +13590,6 @@ snapshots:
 
   is-decimal@2.0.1: {}
 
-  is-docker@2.2.1: {}
-
   is-docker@3.0.0: {}
 
   is-extglob@2.1.1: {}
@@ -13640,10 +13623,6 @@ snapshots:
 
   is-unsafe@2.0.0: {}
 
-  is-wsl@2.2.0:
-    dependencies:
-      is-docker: 2.2.1
-
   is-wsl@3.1.1:
     dependencies:
       is-inside-container: 1.0.0
@@ -13670,12 +13649,6 @@ snapshots:
       html-escaper: 2.0.2
       istanbul-lib-report: 3.0.1
 
-  jake@10.9.4:
-    dependencies:
-      async: 3.2.6
-      filelist: 1.0.6
-      picocolors: 1.1.1
-
   jiti@2.7.0: {}
 
   jju@1.4.0: {}
@@ -14793,7 +14766,7 @@ snapshots:
 
   npm-to-yarn@3.2.0: {}
 
-  npm@11.19.0: {}
+  npm@11.21.0: {}
 
   object-assign@4.1.1: {}
 
@@ -15021,6 +14994,8 @@ snapshots:
     dependencies:
       xtend: 4.0.2
 
+  powershell-utils@0.1.0: {}
+
   prebuild-install@7.1.3:
     dependencies:
       detect-libc: 2.1.2
@@ -16192,6 +16167,11 @@ snapshots:
     dependencies:
       is-wsl: 3.1.1
 
+  wsl-utils@0.4.0:
+    dependencies:
+      is-wsl: 3.1.1
+      powershell-utils: 0.1.0
+
   xml-crypto@6.1.2:
     dependencies:
       '@xmldom/is-dom-node': 1.0.1
diff --git a/scripts/check-cli-command-ids.mjs b/scripts/check-cli-command-ids.mjs
index 931f6e10ccc..a7db333dfc6 100644
--- a/scripts/check-cli-command-ids.mjs
+++ b/scripts/check-cli-command-ids.mjs
@@ -382,7 +382,7 @@ export function binNamesOf(pkg) {
  * `os` invocation, whatever the user actually ran:
  *
  *     (node:1922) Warning: Error
- *     module: @oclif/core@4.13.3
+ *     module: @oclif/core@5.1.2
  *     task: findCommand (migrate:file-column-move)
  *     plugin: @objectstack/cli
  *     message: command migrate:file-column-move not found
diff --git a/scripts/check-cli-test-child-env.mjs b/scripts/check-cli-test-child-env.mjs
index f1466509642..45c40db8077 100644
--- a/scripts/check-cli-test-child-env.mjs
+++ b/scripts/check-cli-test-child-env.mjs
@@ -184,8 +184,8 @@
  * is a no-op with a false comment attached: `dist/` is never executed, the
  * suite stays green, and the comment claiming the built entry stays plausible.
  *
- * `@oclif/core@4.13.3` skips its TypeScript path lookup only when `isProd()`,
- * which its `lib/util/util.js` (line 66 as pinned -- a dependency file, outside
+ * `@oclif/core@5.1.2` skips its TypeScript path lookup only when `isProd()`,
+ * which its `lib/util/util.js` (line 65 as pinned -- a dependency file, outside
  * this tree) defines as a NEGATED membership test -- a leading
  * logical-NOT over `['development', 'test'].includes(process.env.NODE_ENV ?? '')`.
  * Measured directly against `Config.load()` on `packages/cli`, with
@@ -1090,8 +1090,8 @@ const BUILT_ENTRYPOINT = 'bin/run.js';
 /**
  * The `NODE_ENV` values that send `@oclif/core`'s command lookup to `src/`.
  *
- * `@oclif/core@4.13.3` skips its TypeScript path lookup only when `isProd()`,
- * which its `lib/util/util.js` (line 66 as pinned -- a dependency file, outside
+ * `@oclif/core@5.1.2` skips its TypeScript path lookup only when `isProd()`,
+ * which its `lib/util/util.js` (line 65 as pinned -- a dependency file, outside
  * this tree) defines as a NEGATED membership test:
  * `!['development', 'test'].includes(process.env.NODE_ENV ?? '')`. So these two
  * values -- and only these two -- turn the reroute ON. `production` and unset
@@ -1597,7 +1597,7 @@ function main() {
       + '\n    is `development` or `test` is asking @oclif/core to resolve those commands'
       + '\n    from src/ instead and transpile them on the fly. Asking for both cancels:'
       + '\n    dist/ is never executed, and the comment claiming the built entry stays'
-      + '\n    plausible. Measured against @oclif/core@4.13.3\'s own Config.load(), reading'
+      + '\n    plausible. Measured against @oclif/core@5.1.2\'s own Config.load(), reading'
       + '\n    back the root plugin\'s resolved commandsDir:'
       + '\n'
       + '\n      NODE_ENV unset        -> packages/cli/dist/commands'
@@ -1605,7 +1605,7 @@ function main() {
       + '\n      NODE_ENV=development  -> packages/cli/src/commands'
       + '\n      NODE_ENV=test         -> packages/cli/src/commands'
       + '\n'
-      + '\n    lib/util/util.js:66 defines isProd() as a NEGATED membership test --'
+      + '\n    lib/util/util.js:65 defines isProd() as a NEGATED membership test --'
       + '\n    !["development","test"].includes(process.env.NODE_ENV ?? "") -- and the'
       + '\n    TypeScript path lookup is skipped only when that is true.'
       + '\n'