diff --git a/.changeset/deepseek-install-pnpm-path.md b/.changeset/deepseek-install-pnpm-path.md
new file mode 100644
index 00000000..48ce0d8f
--- /dev/null
+++ b/.changeset/deepseek-install-pnpm-path.md
@@ -0,0 +1,5 @@
+---
+'aicodeman': patch
+---
+
+Installing DeepSeek from CLI management no longer leaves it "not installed". The `dsh` terminal profile install ran `dsh plugin`, which needs `pnpm` on its PATH, but the server's own PATH usually lacks the user prefix (`~/.local/bin`) where CLI management puts `dsh`. The profile install now puts `dsh`'s directory first on PATH, and the DeepSeek install command installs `pnpm` alongside `dsh` when none is on PATH (an existing one, such as a corepack shim, is left alone: `npm install -g pnpm` refuses to overwrite it).
diff --git a/config/clis.stock.json b/config/clis.stock.json
index 5a86af0e..c213976b 100644
--- a/config/clis.stock.json
+++ b/config/clis.stock.json
@@ -238,8 +238,8 @@
       },
       "install": {
         "command": {
-          "linux": "npm install -g @deepseek-ai/dsh",
-          "darwin": "npm install -g @deepseek-ai/dsh"
+          "linux": "npm install -g @deepseek-ai/dsh && (command -v pnpm >/dev/null || npm install -g pnpm)",
+          "darwin": "npm install -g @deepseek-ai/dsh && (command -v pnpm >/dev/null || npm install -g pnpm)"
         },
         "npmPackage": "@deepseek-ai/dsh",
         "docsUrl": "https://github.com/deepseek-ai/deepseek-harness",
diff --git a/src/config/cli-registry/stock.ts b/src/config/cli-registry/stock.ts
index 3075e36f..0a29a74c 100644
--- a/src/config/cli-registry/stock.ts
+++ b/src/config/cli-registry/stock.ts
@@ -1300,8 +1300,14 @@ const DEEPSEEK: CliEntry = {
     launcherTargetParam: 'profile',
     install: {
       command: {
-        linux: 'npm install -g @deepseek-ai/dsh',
-        darwin: 'npm install -g @deepseek-ai/dsh',
+        // pnpm rides along: `dsh plugin` spawns a literal `pnpm` with no npm fallback, so the
+        // terminal profile this CLI needs before it can run cannot be installed without it (#352).
+        // ⚠️ Only when none is on PATH. `corepack enable` puts a `pnpm` shim in node's own bin
+        // directory, which is npm's global bin for nvm and Homebrew, and `npm install -g pnpm`
+        // refuses to overwrite it (EEXIST). Asked for in the same command as dsh, that failure
+        // took dsh down with it, on exactly the machines that already had a working pnpm.
+        linux: 'npm install -g @deepseek-ai/dsh && (command -v pnpm >/dev/null || npm install -g pnpm)',
+        darwin: 'npm install -g @deepseek-ai/dsh && (command -v pnpm >/dev/null || npm install -g pnpm)',
       },
       npmPackage: '@deepseek-ai/dsh',
       docsUrl: 'https://github.com/deepseek-ai/deepseek-harness',
diff --git a/src/utils/deepseek-cli-resolver.ts b/src/utils/deepseek-cli-resolver.ts
index b815a761..498967aa 100644
--- a/src/utils/deepseek-cli-resolver.ts
+++ b/src/utils/deepseek-cli-resolver.ts
@@ -84,7 +84,8 @@ export const DEEPSEEK_VERSION_REGEX = /(?:^|\s)v?(\d+\.\d+\.\d+(?:-[0-9A-Za-z][0
  */
 export const DEEPSEEK_IDENTITY_REGEX = /DeepSeek\s+Harness/i;
 
-const DEEPSEEK_NOT_FOUND = 'DeepSeek Harness CLI (dsh) not found. Install with: npm install -g @deepseek-ai/dsh';
+const DEEPSEEK_NOT_FOUND =
+  'DeepSeek Harness CLI (dsh) not found. Install with: npm install -g @deepseek-ai/dsh && (command -v pnpm >/dev/null || npm install -g pnpm)';
 
 /** Where profiles live: `$DSH_HOME/profiles`, defaulting to `~/.dsh/profiles`. */
 export function resolveDshHome(): string {
diff --git a/src/web/public/session-ui.js b/src/web/public/session-ui.js
index 9e32f0b0..71345763 100644
--- a/src/web/public/session-ui.js
+++ b/src/web/public/session-ui.js
@@ -92,7 +92,7 @@ const RUN_MODE_LAUNCH = {
   },
   deepseek: {
     label: 'DeepSeek',
-    installHint: 'DeepSeek Harness CLI (dsh) not found. Install with: npm install -g @deepseek-ai/dsh',
+    installHint: 'DeepSeek Harness CLI (dsh) not found. Install with: npm install -g @deepseek-ai/dsh && (command -v pnpm >/dev/null || npm install -g pnpm)',
     // The two-part availability check is deliberate. `dsh` being installed is
     // not enough — DeepSeek ships no terminal front door, so a box can have a
     // perfect binary and nothing a pane can run.
diff --git a/src/web/routes/system-routes.ts b/src/web/routes/system-routes.ts
index e2251c24..91f49b04 100644
--- a/src/web/routes/system-routes.ts
+++ b/src/web/routes/system-routes.ts
@@ -617,13 +617,16 @@ export function registerSystemRoutes(
           // synchronous-spawn precedent this endpoint is modelled on.
           detached: true,
           // Inherit the environment: this needs a HOME to resolve $DSH_HOME
-          // against, and a PATH carrying `pnpm`. ⚠️ `dsh plugin` does NOT bundle a
+          // against, and a PATH carrying `pnpm` (see the PATH below). ⚠️ `dsh plugin` does NOT bundle a
           // package manager — it `spawnSync`s a literal `pnpm` with no npm
           // fallback, so on a host without one this exits 127 and dsh's own
           // stderr ("pnpm not found on PATH") is what reaches the caller through
           // the OPERATION_FAILED detail below. That is the same missing
           // dependency that broke the docker agent image in issue #352.
-          env: process.env,
+          // PATH leads with the directory `dsh` itself resolved to: CLI management installs
+          // `dsh` and `pnpm` into the user prefix (`~/.local/bin`), which a service's own PATH
+          // usually lacks, so `dsh plugin` could not find the `pnpm` sitting next to it.
+          env: { ...process.env, PATH: [dir, process.env.PATH].filter(Boolean).join(':') },
         });
       } catch (err) {
         resolve({ code: null, output: `spawn failed: ${getErrorMessage(err)}`, timedOut: false });
diff --git a/test/deepseek-install-profile-path.test.ts b/test/deepseek-install-profile-path.test.ts
new file mode 100644
index 00000000..159f778f
--- /dev/null
+++ b/test/deepseek-install-profile-path.test.ts
@@ -0,0 +1,76 @@
+import { describe, it, expect, afterEach } from 'vitest';
+import { chmodSync, mkdirSync, mkdtempSync, readFileSync, rmSync, writeFileSync } from 'node:fs';
+import { spawnSync } from 'node:child_process';
+import { tmpdir } from 'node:os';
+import { join, resolve } from 'node:path';
+import { STOCK_CLIS } from '../src/config/cli-registry/stock.js';
+
+const root = resolve(import.meta.dirname, '..');
+const dirs: string[] = [];
+afterEach(() => {
+  for (const dir of dirs.splice(0)) rmSync(dir, { recursive: true, force: true });
+});
+
+function deepseekInstallCommand(platform: 'linux' | 'darwin'): string {
+  const ds = STOCK_CLIS.find((c) => (c.id as string) === 'deepseek')!;
+  return ds.discovery.install.command![platform]!;
+}
+
+/**
+ * Run the stock install command through `/bin/sh -c` (what CLI management does, `shell: true`)
+ * with a fake `npm` that records each call, on a PATH that holds only the fake bins. So this
+ * exercises the real string, not a copy of it.
+ */
+function runInstall(opts: { pnpmOnPath: boolean; npmFails?: boolean }): { status: number | null; npmCalls: string[] } {
+  const dir = mkdtempSync(join(tmpdir(), 'dsh-install-'));
+  dirs.push(dir);
+  const npmBin = join(dir, 'npm-bin');
+  const pnpmBin = join(dir, 'pnpm-bin');
+  mkdirSync(npmBin);
+  mkdirSync(pnpmBin);
+  const log = join(dir, 'npm.log');
+  writeFileSync(log, '');
+  writeFileSync(join(npmBin, 'npm'), '#!/bin/sh\necho "$*" >> "$NPM_LOG"\nexit "${NPM_EXIT:-0}"\n');
+  chmodSync(join(npmBin, 'npm'), 0o755);
+  writeFileSync(join(pnpmBin, 'pnpm'), '#!/bin/sh\nexit 0\n');
+  chmodSync(join(pnpmBin, 'pnpm'), 0o755);
+  const result = spawnSync('/bin/sh', ['-c', deepseekInstallCommand('linux')], {
+    env: {
+      PATH: opts.pnpmOnPath ? `${npmBin}:${pnpmBin}` : npmBin,
+      NPM_LOG: log,
+      NPM_EXIT: opts.npmFails ? '1' : '0',
+    },
+    encoding: 'utf-8',
+  });
+  const npmCalls = readFileSync(log, 'utf-8').split('\n').filter(Boolean);
+  return { status: result.status, npmCalls };
+}
+
+describe('DeepSeek install', () => {
+  it('is the same command on linux and darwin', () => {
+    expect(deepseekInstallCommand('darwin')).toBe(deepseekInstallCommand('linux'));
+  });
+
+  it('installs pnpm with dsh when none is on PATH, since `dsh plugin` spawns a literal pnpm', () => {
+    const { status, npmCalls } = runInstall({ pnpmOnPath: false });
+    expect(status).toBe(0);
+    expect(npmCalls).toEqual(['install -g @deepseek-ai/dsh', 'install -g pnpm']);
+  });
+
+  it('leaves an existing pnpm alone (a corepack shim makes `npm install -g pnpm` fail with EEXIST)', () => {
+    const { status, npmCalls } = runInstall({ pnpmOnPath: true });
+    expect(status).toBe(0);
+    expect(npmCalls).toEqual(['install -g @deepseek-ai/dsh']);
+  });
+
+  it('reports a failed dsh install and does not go on to pnpm', () => {
+    const { status, npmCalls } = runInstall({ pnpmOnPath: false, npmFails: true });
+    expect(status).not.toBe(0);
+    expect(npmCalls).toEqual(['install -g @deepseek-ai/dsh']);
+  });
+
+  it("puts dsh's own directory first on the profile install's PATH", () => {
+    const src = readFileSync(resolve(root, 'src/web/routes/system-routes.ts'), 'utf8');
+    expect(src).toMatch(/env: \{ \.\.\.process\.env, PATH: \[dir, process\.env\.PATH\]/);
+  });
+});