diff --git a/packages/adapter-utils/src/command-managed-runtime.ts b/packages/adapter-utils/src/command-managed-runtime.ts
index 844fc31d..78d7c020 100644
--- a/packages/adapter-utils/src/command-managed-runtime.ts
+++ b/packages/adapter-utils/src/command-managed-runtime.ts
@@ -144,6 +144,8 @@ export async function prepareCommandManagedRuntime(input: {
   preserveAbsentOnRestore?: string[];
   assets?: CommandManagedRuntimeAsset[];
   installCommand?: string | null;
+  /** When provided alongside `installCommand`, skip the install if `command -v <detectCommand>` succeeds. */
+  detectCommand?: string | null;
 }): Promise<PreparedSandboxManagedRuntime> {
   const timeoutMs = input.spec.timeoutMs && input.spec.timeoutMs > 0 ? input.spec.timeoutMs : 300_000;
   const workspaceRemoteDir = input.workspaceRemoteDir ?? input.spec.remoteCwd;
@@ -164,13 +166,52 @@ export async function prepareCommandManagedRuntime(input: {
   const shellCommand = preferredShellForSandbox(input.spec.shellCommand);
 
   if (input.installCommand?.trim()) {
+    const installCommand = input.installCommand.trim();
+    const detectCommand = input.detectCommand?.trim();
+    // Skip the install when the binary is already on PATH. Without this
+    // probe the install runs unconditionally on every execute() call (and
+    // also runs a second time after `ensureAdapterExecutionTargetCommandResolvable`
+    // has already installed it during the resolvability gate).
+    if (detectCommand) {
+      const probe = await input.runner.execute({
+        command: shellCommand,
+        args: ["-lc", `command -v ${shellQuote(detectCommand)} >/dev/null 2>&1`],
+        cwd: workspaceRemoteDir,
+        timeoutMs,
+      });
+      if (!probe.timedOut && (probe.exitCode ?? 1) === 0) {
+        return await prepareSandboxManagedRuntime({
+          spec: runtimeSpec,
+          client,
+          adapterKey: input.adapterKey,
+          workspaceLocalDir: input.workspaceLocalDir,
+          workspaceRemoteDir,
+          workspaceExclude: mergeRuntimeExcludes(input.workspaceExclude),
+          preserveAbsentOnRestore: input.preserveAbsentOnRestore,
+          assets: input.assets,
+        });
+      }
+    }
     const result = await input.runner.execute({
       command: shellCommand,
-      args: ["-lc", input.installCommand.trim()],
+      args: ["-lc", installCommand],
       cwd: workspaceRemoteDir,
       timeoutMs,
     });
-    requireSuccessfulResult(result, input.installCommand.trim());
+    // A failed install is not always fatal: the CLI may already be on PATH
+    // from a previous lease, the template image, or another path entry. Log
+    // and continue rather than aborting the agent run; downstream code that
+    // exec's the CLI will surface a clear "command not found" if it is in
+    // fact missing. The test path's `maybeRunSandboxInstallCommand` already
+    // honors this contract — keep them consistent.
+    if (result.timedOut || (result.exitCode ?? 0) !== 0) {
+      const tail = (text: string) =>
+        text.split(/\r?\n/).filter((line) => line.trim().length > 0).slice(-3).join(" | ").slice(0, 480);
+      const reason = result.timedOut ? "timed out" : `exited ${result.exitCode ?? "?"}`;
+      console.warn(
+        `[paperclip] managed-runtime install command ${reason}: ${installCommand} :: ${tail(result.stderr || result.stdout)}`,
+      );
+    }
   }
 
   return await prepareSandboxManagedRuntime({
diff --git a/packages/adapter-utils/src/execution-target.ts b/packages/adapter-utils/src/execution-target.ts
index 06445a2c..563d1795 100644
--- a/packages/adapter-utils/src/execution-target.ts
+++ b/packages/adapter-utils/src/execution-target.ts
@@ -230,9 +230,10 @@ export async function ensureAdapterExecutionTargetCommandResolvable(
   target: AdapterExecutionTarget | null | undefined,
   cwd: string,
   env: NodeJS.ProcessEnv,
+  options: { installCommand?: string | null } = {},
 ) {
   if (target?.kind === "remote" && target.transport === "sandbox") {
-    await ensureSandboxCommandResolvable(command, target);
+    await ensureSandboxCommandResolvable(command, target, options.installCommand?.trim() || null);
     return;
   }
   await ensureCommandResolvable(command, cwd, env, {
@@ -240,17 +241,10 @@ export async function ensureAdapterExecutionTargetCommandResolvable(
   });
 }
 
-async function ensureSandboxCommandResolvable(
+async function probeSandboxCommandResolvable(
   command: string,
   target: AdapterSandboxExecutionTarget,
-): Promise<void> {
-  // Probe whether the binary is resolvable inside the sandbox. We previously
-  // short-circuited this for sandbox targets, which let the caller report a
-  // success message even when the CLI was missing from the image. Now we run
-  // a real `command -v` through the same runner the hello probe will use, so
-  // the first step honestly reflects whether the binary is on PATH. The
-  // sandbox provider is responsible for sourcing login profiles (e2b mirrors
-  // SSH's buildSshSpawnTarget) so this and the hello probe agree on PATH.
+): Promise<{ resolved: boolean; timedOut: boolean; stderr: string }> {
   const runner = requireSandboxRunner(target);
   const probeScript = `command -v ${shellQuote(command)}`;
   const result = await runner.execute({
@@ -259,14 +253,67 @@ async function ensureSandboxCommandResolvable(
     cwd: target.remoteCwd,
     timeoutMs: target.timeoutMs ?? 15_000,
   });
-  if (result.timedOut) {
+  return {
+    resolved: !result.timedOut && (result.exitCode ?? 1) === 0,
+    timedOut: result.timedOut,
+    stderr: result.stderr.trim(),
+  };
+}
+
+async function ensureSandboxCommandResolvable(
+  command: string,
+  target: AdapterSandboxExecutionTarget,
+  installCommand: string | null,
+): Promise<void> {
+  // Probe whether the binary is resolvable inside the sandbox. We previously
+  // short-circuited this for sandbox targets, which let the caller report a
+  // success message even when the CLI was missing from the image. Now we run
+  // a real `command -v` through the same runner the hello probe will use, so
+  // the first step honestly reflects whether the binary is on PATH. The
+  // sandbox provider is responsible for sourcing login profiles (e2b mirrors
+  // SSH's buildSshSpawnTarget) so this and the hello probe agree on PATH.
+  let probe = await probeSandboxCommandResolvable(command, target);
+  if (probe.resolved) return;
+  if (probe.timedOut) {
     throw new Error(`Timed out checking command "${command}" on sandbox target.`);
   }
-  if ((result.exitCode ?? 1) === 0) return;
-  const stderr = result.stderr.trim();
-  const detail = stderr.length > 0 ? ` (${stderr})` : "";
+
+  // If the caller supplied an install command, attempt the install once via
+  // the sandbox runner (which the sandbox provider wraps in a login shell)
+  // and re-probe before reporting failure. This lets fresh sandbox leases
+  // bring up the CLI before the resolvability gate, mirroring the test path.
+  let installFailureDetail: string | null = null;
+  if (installCommand) {
+    const runner = requireSandboxRunner(target);
+    try {
+      const installResult = await runner.execute({
+        command: "sh",
+        args: ["-lc", installCommand],
+        cwd: target.remoteCwd,
+        timeoutMs: target.timeoutMs ?? 300_000,
+      });
+      if (installResult.timedOut) {
+        installFailureDetail = `install command timed out: ${installCommand}`;
+      } else if ((installResult.exitCode ?? 0) !== 0) {
+        const tail = (text: string) =>
+          text.split(/\r?\n/).filter((line) => line.trim().length > 0).slice(-2).join(" | ").slice(0, 240);
+        const reason = tail(installResult.stderr || installResult.stdout) || `exit ${installResult.exitCode ?? "?"}`;
+        installFailureDetail = `install command exited ${installResult.exitCode ?? "?"}: ${reason}`;
+      }
+    } catch (err) {
+      installFailureDetail = `install command threw: ${err instanceof Error ? err.message : String(err)}`;
+    }
+    probe = await probeSandboxCommandResolvable(command, target);
+    if (probe.resolved) return;
+    if (probe.timedOut) {
+      throw new Error(`Timed out checking command "${command}" on sandbox target.`);
+    }
+  }
+
+  const probeStderr = probe.stderr.length > 0 ? ` probe stderr: ${probe.stderr}` : "";
+  const installDetail = installFailureDetail ? `; ${installFailureDetail}` : "";
   throw new Error(
-    `Command "${command}" is not installed or not on PATH in the sandbox environment${detail}.`,
+    `Command "${command}" is not installed or not on PATH in the sandbox environment${installDetail}.${probeStderr}`,
   );
 }
 
@@ -409,6 +456,111 @@ export async function runAdapterExecutionTargetShellCommand(
   );
 }
 
+export interface AdapterSandboxInstallCommandCheck {
+  code: string;
+  level: "info" | "warn" | "error";
+  message: string;
+  detail?: string;
+  hint?: string;
+}
+
+// Best-effort run of an adapter-supplied install command on a sandbox target
+// before the resolvability + hello probe. Returns null for non-sandbox
+// targets so callers can no-op. Returns a structured check otherwise — never
+// throws — so the rest of the test still runs and reports the post-install
+// state honestly. Caller pushes the check into its result array; the test
+// report shows whether install was attempted and what came back.
+export async function maybeRunSandboxInstallCommand(input: {
+  runId: string;
+  target: AdapterExecutionTarget | null | undefined;
+  adapterKey: string;
+  installCommand: string;
+  /** When provided, skip the install if `command -v <detectCommand>` succeeds. */
+  detectCommand?: string | null;
+  env?: Record<string, string>;
+  timeoutSec?: number;
+}): Promise<AdapterSandboxInstallCommandCheck | null> {
+  const { target, adapterKey, installCommand } = input;
+  if (!target || target.kind !== "remote" || target.transport !== "sandbox") {
+    return null;
+  }
+  const trimmed = installCommand.trim();
+  if (trimmed.length === 0) return null;
+
+  const code = `${adapterKey}_install_command_run`;
+
+  // Skip install when the binary is already on PATH. Avoids running
+  // network-dependent installers (e.g. `curl ... | bash`) on every test
+  // probe when the CLI is preinstalled on the lease/template.
+  const detectCommand = input.detectCommand?.trim();
+  if (detectCommand) {
+    try {
+      const probe = await runAdapterExecutionTargetShellCommand(
+        input.runId,
+        target,
+        `command -v ${shellQuote(detectCommand)} >/dev/null 2>&1`,
+        {
+          cwd: target.remoteCwd,
+          env: input.env ?? {},
+          timeoutSec: 30,
+          graceSec: 5,
+        },
+      );
+      if (!probe.timedOut && probe.exitCode === 0) {
+        return {
+          code,
+          level: "info",
+          message: `${detectCommand} already on PATH; skipped install.`,
+        };
+      }
+    } catch {
+      // Fall through to actually running the install — failure to probe
+      // is not a reason to skip the install gate.
+    }
+  }
+
+  let result;
+  try {
+    result = await runAdapterExecutionTargetShellCommand(input.runId, target, trimmed, {
+      cwd: target.remoteCwd,
+      env: input.env ?? {},
+      timeoutSec: input.timeoutSec ?? 240,
+      graceSec: 10,
+    });
+  } catch (err) {
+    return {
+      code,
+      level: "warn",
+      message: "Install command threw before completion.",
+      detail: err instanceof Error ? err.message : String(err),
+    };
+  }
+  const tail = (text: string) =>
+    text.split(/\r?\n/).filter((line) => line.trim().length > 0).slice(-3).join(" | ").slice(0, 480);
+  if (result.timedOut) {
+    return {
+      code,
+      level: "warn",
+      message: `Install command timed out: ${trimmed}`,
+      detail: tail(result.stderr || result.stdout),
+    };
+  }
+  if ((result.exitCode ?? 1) === 0) {
+    return {
+      code,
+      level: "info",
+      message: `Install command ran: ${trimmed}`,
+      ...(tail(result.stdout) ? { detail: tail(result.stdout) } : {}),
+    };
+  }
+  return {
+    code,
+    level: "warn",
+    message: `Install command exited ${result.exitCode}: ${trimmed}`,
+    detail: tail(result.stderr || result.stdout),
+  };
+}
+
 export async function readAdapterExecutionTargetHomeDir(
   runId: string,
   target: AdapterExecutionTarget | null | undefined,
@@ -470,12 +622,43 @@ export async function ensureAdapterExecutionTargetRuntimeCommandInstalled(input:
       onLog: input.onLog,
     },
   );
+
+  // A failed or timed-out install is not necessarily fatal: the CLI may already
+  // be on PATH from a previous lease's install, the template image, or another
+  // path entry. Re-run the detect probe (when one is configured) so a transient
+  // install failure does not abort the agent run when the binary is reachable.
+  const installFailed = result.timedOut || (result.exitCode ?? 0) !== 0;
+  if (!installFailed) {
+    return;
+  }
+  if (detectCommand) {
+    const recheck = await runAdapterExecutionTargetShellCommand(
+      input.runId,
+      input.target,
+      `command -v ${shellQuote(detectCommand)} >/dev/null 2>&1`,
+      {
+        cwd: input.cwd,
+        env: input.env,
+        timeoutSec: input.timeoutSec,
+        graceSec: input.graceSec,
+      },
+    );
+    if (!recheck.timedOut && recheck.exitCode === 0) {
+      if (input.onLog) {
+        const reason = result.timedOut ? "timed out" : `exited ${result.exitCode ?? "?"}`;
+        await input.onLog(
+          "stderr",
+          `[paperclip] Install command ${reason} (${installCommand}) but ${detectCommand} is on PATH; continuing.\n`,
+        );
+      }
+      return;
+    }
+  }
+
   if (result.timedOut) {
     throw new Error(`Timed out while installing the adapter runtime command via: ${installCommand}`);
   }
-  if ((result.exitCode ?? 0) !== 0) {
-    throw new Error(`Failed to install the adapter runtime command via: ${installCommand}`);
-  }
+  throw new Error(`Failed to install the adapter runtime command via: ${installCommand}`);
 }
 
 export async function ensureAdapterExecutionTargetFile(
@@ -666,6 +849,8 @@ export async function prepareAdapterExecutionTargetRuntime(input: {
   preserveAbsentOnRestore?: string[];
   assets?: AdapterManagedRuntimeAsset[];
   installCommand?: string | null;
+  /** When provided alongside `installCommand`, skip the install if the binary is already on PATH. */
+  detectCommand?: string | null;
 }): Promise<PreparedAdapterExecutionTargetRuntime> {
   const target = input.target ?? { kind: "local" as const };
   if (target.kind === "local") {
@@ -707,6 +892,7 @@ export async function prepareAdapterExecutionTargetRuntime(input: {
     preserveAbsentOnRestore: input.preserveAbsentOnRestore,
     assets: input.assets,
     installCommand: input.installCommand,
+    detectCommand: input.detectCommand,
   });
   return {
     target,
diff --git a/packages/adapters/claude-local/src/index.ts b/packages/adapters/claude-local/src/index.ts
index 9b928ae2..8ad60fa5 100644
--- a/packages/adapters/claude-local/src/index.ts
+++ b/packages/adapters/claude-local/src/index.ts
@@ -3,6 +3,8 @@ import type { AdapterModelProfileDefinition } from "@paperclipai/adapter-utils";
 export const type = "claude_local";
 export const label = "Claude Code (local)";
 
+export const SANDBOX_INSTALL_COMMAND = "npm install -g @anthropic-ai/claude-code";
+
 export const models = [
   { id: "claude-opus-4-7", label: "Claude Opus 4.7" },
   { id: "claude-opus-4-6", label: "Claude Opus 4.6" },
diff --git a/packages/adapters/claude-local/src/server/execute.ts b/packages/adapters/claude-local/src/server/execute.ts
index cd3ed45c..19daae24 100644
--- a/packages/adapters/claude-local/src/server/execute.ts
+++ b/packages/adapters/claude-local/src/server/execute.ts
@@ -54,6 +54,7 @@ import { prepareClaudeConfigSeed } from "./claude-config.js";
 import { resolveClaudeDesiredSkillNames } from "./skills.js";
 import { isBedrockModelId } from "./models.js";
 import { prepareClaudePromptBundle } from "./prompt-cache.js";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
 
 const __moduleDir = path.dirname(fileURLToPath(import.meta.url));
 
@@ -261,7 +262,7 @@ async function buildClaudeRuntimeConfig(input: ClaudeExecutionInput): Promise<Cl
     graceSec,
     onLog,
   });
-  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv);
+  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv, { installCommand: SANDBOX_INSTALL_COMMAND });
   const resolvedCommand = await resolveAdapterExecutionTargetCommandForLogs(command, executionTarget, cwd, runtimeEnv);
   const loggedEnv = buildInvocationEnvForLogs(env, {
     runtimeEnv,
@@ -430,6 +431,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
           target: executionTarget,
           adapterKey: "claude",
           workspaceLocalDir: cwd,
+          installCommand: SANDBOX_INSTALL_COMMAND,
+          detectCommand: command,
           assets: [
             {
               key: "skills",
diff --git a/packages/adapters/claude-local/src/server/test.ts b/packages/adapters/claude-local/src/server/test.ts
index ba736c8a..f4d80a20 100644
--- a/packages/adapters/claude-local/src/server/test.ts
+++ b/packages/adapters/claude-local/src/server/test.ts
@@ -14,6 +14,7 @@ import {
 import {
   ensureAdapterExecutionTargetCommandResolvable,
   ensureAdapterExecutionTargetDirectory,
+  maybeRunSandboxInstallCommand,
   runAdapterExecutionTargetProcess,
   describeAdapterExecutionTarget,
   resolveAdapterExecutionTargetCwd,
@@ -21,6 +22,7 @@ import {
 import path from "node:path";
 import { detectClaudeLoginRequired, parseClaudeStreamJson } from "./parse.js";
 import { isBedrockModelId } from "./models.js";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
 
 function summarizeStatus(checks: AdapterEnvironmentCheck[]): AdapterEnvironmentTestResult["status"] {
   if (checks.some((check) => check.level === "error")) return "fail";
@@ -102,6 +104,15 @@ export async function testEnvironment(
     if (typeof value === "string") env[key] = value;
   }
   const runtimeEnv = ensurePathInEnv({ ...process.env, ...env });
+  const installCheck = await maybeRunSandboxInstallCommand({
+    runId,
+    target,
+    adapterKey: "claude",
+    installCommand: SANDBOX_INSTALL_COMMAND,
+    detectCommand: command,
+    env,
+  });
+  if (installCheck) checks.push(installCheck);
   try {
     await ensureAdapterExecutionTargetCommandResolvable(command, target, cwd, runtimeEnv);
     checks.push({
diff --git a/packages/adapters/codex-local/src/index.ts b/packages/adapters/codex-local/src/index.ts
index ae271820..d869dda8 100644
--- a/packages/adapters/codex-local/src/index.ts
+++ b/packages/adapters/codex-local/src/index.ts
@@ -3,6 +3,8 @@ import type { AdapterModelProfileDefinition } from "@paperclipai/adapter-utils";
 export const type = "codex_local";
 export const label = "Codex (local)";
 
+export const SANDBOX_INSTALL_COMMAND = "npm install -g @openai/codex";
+
 export const DEFAULT_CODEX_LOCAL_MODEL = "gpt-5.3-codex";
 export const DEFAULT_CODEX_LOCAL_BYPASS_APPROVALS_AND_SANDBOX = true;
 export const CODEX_LOCAL_FAST_MODE_SUPPORTED_MODELS = ["gpt-5.4"] as const;
diff --git a/packages/adapters/codex-local/src/server/execute.ts b/packages/adapters/codex-local/src/server/execute.ts
index 67c7633d..0c18406f 100644
--- a/packages/adapters/codex-local/src/server/execute.ts
+++ b/packages/adapters/codex-local/src/server/execute.ts
@@ -45,6 +45,7 @@ import {
 import { pathExists, prepareManagedCodexHome, resolveManagedCodexHomeDir, resolveSharedCodexHomeDir } from "./codex-home.js";
 import { resolveCodexDesiredSkillNames } from "./skills.js";
 import { buildCodexExecArgs } from "./codex-args.js";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
 
 const __moduleDir = path.dirname(fileURLToPath(import.meta.url));
 const CODEX_ROLLOUT_NOISE_RE =
@@ -374,6 +375,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
           target: executionTarget,
           adapterKey: "codex",
           workspaceLocalDir: cwd,
+          installCommand: SANDBOX_INSTALL_COMMAND,
+          detectCommand: command,
           assets: [
             {
               key: "home",
diff --git a/packages/adapters/codex-local/src/server/test.ts b/packages/adapters/codex-local/src/server/test.ts
index 98078d57..31b0f73e 100644
--- a/packages/adapters/codex-local/src/server/test.ts
+++ b/packages/adapters/codex-local/src/server/test.ts
@@ -11,6 +11,7 @@ import {
 import {
   ensureAdapterExecutionTargetCommandResolvable,
   ensureAdapterExecutionTargetDirectory,
+  maybeRunSandboxInstallCommand,
   runAdapterExecutionTargetProcess,
   describeAdapterExecutionTarget,
   resolveAdapterExecutionTargetCwd,
@@ -18,6 +19,7 @@ import {
 import path from "node:path";
 import os from "node:os";
 import { parseCodexJsonl } from "./parse.js";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
 import { codexHomeDir, readCodexAuthInfo } from "./quota.js";
 import { buildCodexExecArgs } from "./codex-args.js";
 
@@ -104,6 +106,15 @@ export async function testEnvironment(
     if (typeof value === "string") env[key] = value;
   }
   const runtimeEnv = ensurePathInEnv({ ...process.env, ...env });
+  const installCheck = await maybeRunSandboxInstallCommand({
+    runId,
+    target,
+    adapterKey: "codex",
+    installCommand: SANDBOX_INSTALL_COMMAND,
+    detectCommand: command,
+    env,
+  });
+  if (installCheck) checks.push(installCheck);
   try {
     await ensureAdapterExecutionTargetCommandResolvable(command, target, cwd, runtimeEnv);
     checks.push({
diff --git a/packages/adapters/cursor-local/src/index.ts b/packages/adapters/cursor-local/src/index.ts
index 16fbda54..5c4e2356 100644
--- a/packages/adapters/cursor-local/src/index.ts
+++ b/packages/adapters/cursor-local/src/index.ts
@@ -3,6 +3,15 @@ import type { AdapterModelProfileDefinition } from "@paperclipai/adapter-utils";
 export const type = "cursor";
 export const label = "Cursor CLI (local)";
 
+// Cursor CLI is not distributed as an npm package — the official install
+// path is the upstream installer script at cursor.com/install. Other adapters
+// in this repo prefer `npm install -g <pkg>` which is content-addressed by the
+// registry; cursor must use `curl | bash` until upstream publishes a registry
+// artifact. Pinning a commit/version here would require shipping our own
+// mirror of the installer; revisit if Cursor adds an npm/release-asset
+// equivalent.
+export const SANDBOX_INSTALL_COMMAND = "curl https://cursor.com/install -fsS | bash";
+
 export const DEFAULT_CURSOR_LOCAL_MODEL = "auto";
 
 const CURSOR_FALLBACK_MODEL_IDS = [
diff --git a/packages/adapters/cursor-local/src/server/execute.ts b/packages/adapters/cursor-local/src/server/execute.ts
index 62147e6c..6611fafa 100644
--- a/packages/adapters/cursor-local/src/server/execute.ts
+++ b/packages/adapters/cursor-local/src/server/execute.ts
@@ -42,7 +42,7 @@ import {
   DEFAULT_PAPERCLIP_AGENT_PROMPT_TEMPLATE,
   joinPromptSections,
 } from "@paperclipai/adapter-utils/server-utils";
-import { DEFAULT_CURSOR_LOCAL_MODEL } from "../index.js";
+import { DEFAULT_CURSOR_LOCAL_MODEL, SANDBOX_INSTALL_COMMAND } from "../index.js";
 import { parseCursorJsonl, isCursorUnknownSessionError } from "./parse.js";
 import { prepareCursorSandboxCommand } from "./remote-command.js";
 import { normalizeCursorStreamLine } from "../shared/stream.js";
@@ -340,7 +340,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
   );
   const billingType = resolveCursorBillingType(effectiveEnv);
   const runtimeEnv = ensurePathInEnv(effectiveEnv);
-  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv);
+  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv, { installCommand: SANDBOX_INSTALL_COMMAND });
   const resolvedCommand = await resolveAdapterExecutionTargetCommandForLogs(command, executionTarget, cwd, runtimeEnv);
   let loggedEnv = buildInvocationEnvForLogs(env, {
     runtimeEnv,
@@ -370,6 +370,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         target: executionTarget,
         adapterKey: "cursor",
         workspaceLocalDir: cwd,
+        installCommand: SANDBOX_INSTALL_COMMAND,
+        detectCommand: command,
         assets: [{
           key: "skills",
           localDir: localSkillsDir,
diff --git a/packages/adapters/cursor-local/src/server/test.ts b/packages/adapters/cursor-local/src/server/test.ts
index 0ba5ee67..7155d855 100644
--- a/packages/adapters/cursor-local/src/server/test.ts
+++ b/packages/adapters/cursor-local/src/server/test.ts
@@ -12,6 +12,7 @@ import {
 import {
   ensureAdapterExecutionTargetCommandResolvable,
   ensureAdapterExecutionTargetDirectory,
+  maybeRunSandboxInstallCommand,
   runAdapterExecutionTargetProcess,
   describeAdapterExecutionTarget,
   resolveAdapterExecutionTargetCwd,
@@ -19,7 +20,7 @@ import {
 import fs from "node:fs/promises";
 import os from "node:os";
 import path from "node:path";
-import { DEFAULT_CURSOR_LOCAL_MODEL } from "../index.js";
+import { DEFAULT_CURSOR_LOCAL_MODEL, SANDBOX_INSTALL_COMMAND } from "../index.js";
 import { parseCursorJsonl } from "./parse.js";
 import { isDefaultCursorCommand, prepareCursorSandboxCommand } from "./remote-command.js";
 import { hasCursorTrustBypassArg } from "../shared/trust.js";
@@ -148,6 +149,15 @@ export async function testEnvironment(
   command = sandboxCommand.command;
   env = sandboxCommand.env;
   const runtimeEnv = ensurePathInEnv({ ...process.env, ...env });
+  const installCheck = await maybeRunSandboxInstallCommand({
+    runId,
+    target,
+    adapterKey: "cursor",
+    installCommand: SANDBOX_INSTALL_COMMAND,
+    detectCommand: command,
+    env,
+  });
+  if (installCheck) checks.push(installCheck);
   try {
     await ensureAdapterExecutionTargetCommandResolvable(command, target, cwd, runtimeEnv);
     checks.push({
diff --git a/packages/adapters/gemini-local/src/index.ts b/packages/adapters/gemini-local/src/index.ts
index 0e7dcbf4..68ca627d 100644
--- a/packages/adapters/gemini-local/src/index.ts
+++ b/packages/adapters/gemini-local/src/index.ts
@@ -3,6 +3,8 @@ import type { AdapterModelProfileDefinition } from "@paperclipai/adapter-utils";
 export const type = "gemini_local";
 export const label = "Gemini CLI (local)";
 
+export const SANDBOX_INSTALL_COMMAND = "npm install -g @google/gemini-cli";
+
 export const DEFAULT_GEMINI_LOCAL_MODEL = "auto";
 
 export const models = [
diff --git a/packages/adapters/gemini-local/src/server/execute.ts b/packages/adapters/gemini-local/src/server/execute.ts
index 64a54c0e..cbac9735 100644
--- a/packages/adapters/gemini-local/src/server/execute.ts
+++ b/packages/adapters/gemini-local/src/server/execute.ts
@@ -45,7 +45,7 @@ import {
   DEFAULT_PAPERCLIP_AGENT_PROMPT_TEMPLATE,
   runChildProcess,
 } from "@paperclipai/adapter-utils/server-utils";
-import { DEFAULT_GEMINI_LOCAL_MODEL } from "../index.js";
+import { DEFAULT_GEMINI_LOCAL_MODEL, SANDBOX_INSTALL_COMMAND } from "../index.js";
 import {
   describeGeminiFailure,
   detectGeminiAuthRequired,
@@ -292,7 +292,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     graceSec,
     onLog,
   });
-  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv);
+  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv, { installCommand: SANDBOX_INSTALL_COMMAND });
   const resolvedCommand = await resolveAdapterExecutionTargetCommandForLogs(command, executionTarget, cwd, runtimeEnv);
   let loggedEnv = buildInvocationEnvForLogs(env, {
     runtimeEnv,
@@ -322,6 +322,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         target: executionTarget,
         adapterKey: "gemini",
         workspaceLocalDir: cwd,
+        installCommand: SANDBOX_INSTALL_COMMAND,
+        detectCommand: command,
         assets: [{
           key: "skills",
           localDir: localSkillsDir,
diff --git a/packages/adapters/gemini-local/src/server/test.ts b/packages/adapters/gemini-local/src/server/test.ts
index ec9ef49a..901e5b86 100644
--- a/packages/adapters/gemini-local/src/server/test.ts
+++ b/packages/adapters/gemini-local/src/server/test.ts
@@ -14,12 +14,13 @@ import {
 } from "@paperclipai/adapter-utils/server-utils";
 import {
   ensureAdapterExecutionTargetCommandResolvable,
+  maybeRunSandboxInstallCommand,
   ensureAdapterExecutionTargetDirectory,
   runAdapterExecutionTargetProcess,
   describeAdapterExecutionTarget,
   resolveAdapterExecutionTargetCwd,
 } from "@paperclipai/adapter-utils/execution-target";
-import { DEFAULT_GEMINI_LOCAL_MODEL } from "../index.js";
+import { DEFAULT_GEMINI_LOCAL_MODEL, SANDBOX_INSTALL_COMMAND } from "../index.js";
 import { detectGeminiAuthRequired, detectGeminiQuotaExhausted, parseGeminiJsonl } from "./parse.js";
 import { firstNonEmptyLine } from "./utils.js";
 
@@ -94,6 +95,15 @@ export async function testEnvironment(
     if (typeof value === "string") env[key] = value;
   }
   const runtimeEnv = ensurePathInEnv({ ...process.env, ...env });
+  const installCheck = await maybeRunSandboxInstallCommand({
+    runId,
+    target,
+    adapterKey: "gemini",
+    installCommand: SANDBOX_INSTALL_COMMAND,
+    detectCommand: command,
+    env,
+  });
+  if (installCheck) checks.push(installCheck);
   try {
     await ensureAdapterExecutionTargetCommandResolvable(command, target, cwd, runtimeEnv);
     checks.push({
diff --git a/packages/adapters/opencode-local/src/index.ts b/packages/adapters/opencode-local/src/index.ts
index 885228af..7328e5d3 100644
--- a/packages/adapters/opencode-local/src/index.ts
+++ b/packages/adapters/opencode-local/src/index.ts
@@ -3,6 +3,8 @@ import type { AdapterModelProfileDefinition } from "@paperclipai/adapter-utils";
 export const type = "opencode_local";
 export const label = "OpenCode (local)";
 
+export const SANDBOX_INSTALL_COMMAND = "npm install -g opencode-ai";
+
 export const DEFAULT_OPENCODE_LOCAL_MODEL = "openai/gpt-5.2-codex";
 
 export function isValidOpenCodeModelId(value: unknown): value is string {
diff --git a/packages/adapters/opencode-local/src/server/execute.ts b/packages/adapters/opencode-local/src/server/execute.ts
index a574fba8..08fabe69 100644
--- a/packages/adapters/opencode-local/src/server/execute.ts
+++ b/packages/adapters/opencode-local/src/server/execute.ts
@@ -50,6 +50,7 @@ import {
 } from "./models.js";
 import { removeMaintainerOnlySkillSymlinks } from "@paperclipai/adapter-utils/server-utils";
 import { prepareOpenCodeRuntimeConfig } from "./runtime-config.js";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
 
 const __moduleDir = path.dirname(fileURLToPath(import.meta.url));
 
@@ -316,7 +317,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
       graceSec,
       onLog,
     });
-    await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv);
+    await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv, { installCommand: SANDBOX_INSTALL_COMMAND });
     const resolvedCommand = await resolveAdapterExecutionTargetCommandForLogs(command, executionTarget, cwd, runtimeEnv);
     let loggedEnv = buildInvocationEnvForLogs(preparedRuntimeConfig.env, {
       runtimeEnv,
@@ -352,6 +353,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         target: executionTarget,
         adapterKey: "opencode",
         workspaceLocalDir: cwd,
+        installCommand: SANDBOX_INSTALL_COMMAND,
+        detectCommand: command,
         assets: [
           {
             key: "skills",
diff --git a/packages/adapters/opencode-local/src/server/test.ts b/packages/adapters/opencode-local/src/server/test.ts
index d9d42456..a4758084 100644
--- a/packages/adapters/opencode-local/src/server/test.ts
+++ b/packages/adapters/opencode-local/src/server/test.ts
@@ -12,6 +12,7 @@ import {
 } from "@paperclipai/adapter-utils/server-utils";
 import {
   ensureAdapterExecutionTargetCommandResolvable,
+  maybeRunSandboxInstallCommand,
   ensureAdapterExecutionTargetDirectory,
   runAdapterExecutionTargetProcess,
   describeAdapterExecutionTarget,
@@ -19,6 +20,7 @@ import {
 } from "@paperclipai/adapter-utils/execution-target";
 import { discoverOpenCodeModels, ensureOpenCodeModelConfiguredAndAvailable } from "./models.js";
 import { parseOpenCodeJsonl } from "./parse.js";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
 import { prepareOpenCodeRuntimeConfig } from "./runtime-config.js";
 
 function summarizeStatus(checks: AdapterEnvironmentCheck[]): AdapterEnvironmentTestResult["status"] {
@@ -136,6 +138,15 @@ export async function testEnvironment(
         detail: command,
       });
     } else {
+      const installCheck = await maybeRunSandboxInstallCommand({
+        runId,
+        target,
+        adapterKey: "opencode",
+        installCommand: SANDBOX_INSTALL_COMMAND,
+    detectCommand: command,
+        env,
+      });
+      if (installCheck) checks.push(installCheck);
       try {
         await ensureAdapterExecutionTargetCommandResolvable(command, target, cwd, runtimeEnv);
         checks.push({
diff --git a/packages/adapters/pi-local/src/index.ts b/packages/adapters/pi-local/src/index.ts
index 6daaa59b..4d13eb76 100644
--- a/packages/adapters/pi-local/src/index.ts
+++ b/packages/adapters/pi-local/src/index.ts
@@ -3,6 +3,8 @@ import type { AdapterModelProfileDefinition } from "@paperclipai/adapter-utils";
 export const type = "pi_local";
 export const label = "Pi (local)";
 
+export const SANDBOX_INSTALL_COMMAND = "npm install -g @mariozechner/pi-coding-agent";
+
 export const models: Array<{ id: string; label: string }> = [];
 
 export const modelProfiles: AdapterModelProfileDefinition[] = [];
diff --git a/packages/adapters/pi-local/src/server/execute.ts b/packages/adapters/pi-local/src/server/execute.ts
index feba3790..a89332ae 100644
--- a/packages/adapters/pi-local/src/server/execute.ts
+++ b/packages/adapters/pi-local/src/server/execute.ts
@@ -46,6 +46,7 @@ import {
 import { shellQuote } from "@paperclipai/adapter-utils/ssh";
 import { isPiUnknownSessionError, parsePiJsonl } from "./parse.js";
 import { ensurePiModelConfiguredAndAvailable } from "./models.js";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
 
 const __moduleDir = path.dirname(fileURLToPath(import.meta.url));
 
@@ -361,7 +362,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     graceSec,
     onLog,
   });
-  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv);
+  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv, { installCommand: SANDBOX_INSTALL_COMMAND });
   const resolvedCommand = await resolveAdapterExecutionTargetCommandForLogs(command, executionTarget, cwd, runtimeEnv);
   let loggedEnv = buildInvocationEnvForLogs(env, {
     runtimeEnv,
@@ -400,6 +401,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         target: executionTarget,
         adapterKey: "pi",
         workspaceLocalDir: cwd,
+        installCommand: SANDBOX_INSTALL_COMMAND,
+        detectCommand: command,
         assets: [
           {
             key: "skills",
diff --git a/packages/adapters/pi-local/src/server/test.ts b/packages/adapters/pi-local/src/server/test.ts
index 3ea8dff2..aef648ef 100644
--- a/packages/adapters/pi-local/src/server/test.ts
+++ b/packages/adapters/pi-local/src/server/test.ts
@@ -13,6 +13,7 @@ import {
 } from "@paperclipai/adapter-utils/server-utils";
 import {
   ensureAdapterExecutionTargetCommandResolvable,
+  maybeRunSandboxInstallCommand,
   ensureAdapterExecutionTargetDirectory,
   runAdapterExecutionTargetProcess,
   describeAdapterExecutionTarget,
@@ -20,6 +21,7 @@ import {
 } from "@paperclipai/adapter-utils/execution-target";
 import { discoverPiModelsCached } from "./models.js";
 import { parsePiJsonl } from "./parse.js";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
 
 function summarizeStatus(checks: AdapterEnvironmentCheck[]): AdapterEnvironmentTestResult["status"] {
   if (checks.some((check) => check.level === "error")) return "fail";
@@ -134,6 +136,15 @@ export async function testEnvironment(
       detail: command,
     });
   } else {
+    const installCheck = await maybeRunSandboxInstallCommand({
+      runId,
+      target,
+      adapterKey: "pi",
+      installCommand: SANDBOX_INSTALL_COMMAND,
+    detectCommand: command,
+      env,
+    });
+    if (installCheck) checks.push(installCheck);
     try {
       await ensureAdapterExecutionTargetCommandResolvable(command, target, cwd, runtimeEnv);
       checks.push({