diff --git a/packages/adapters/cursor-local/src/index.ts b/packages/adapters/cursor-local/src/index.ts
index 09d29db4..f93928d8 100644
--- a/packages/adapters/cursor-local/src/index.ts
+++ b/packages/adapters/cursor-local/src/index.ts
@@ -104,5 +104,5 @@ Notes:
 - Sessions are resumed with --resume when stored session cwd matches current cwd.
 - Paperclip auto-injects local skills into "~/.cursor/skills" when missing, so Cursor can discover "$paperclip" and related skills on local runs.
 - Paperclip auto-adds --yolo unless one of --trust/--yolo/-f is already present in extraArgs.
-- Remote sandbox runs prepend "~/.local/bin" to PATH and prefer the installed "~/.local/bin/agent" or "~/.local/bin/cursor-agent" entrypoint when the default Cursor command is requested, so standard E2B-style installs do not need hardcoded absolute command paths.
+- Remote sandbox runs prepend "~/.cursor/bin" and "~/.local/bin" to PATH and prefer the installed absolute entrypoint from one of those directories when the default Cursor command is requested, so installer-managed sandbox leases do not need hardcoded command paths.
 `;
diff --git a/packages/adapters/cursor-local/src/server/execute.test.ts b/packages/adapters/cursor-local/src/server/execute.test.ts
index d83101ab..d0d8ce4b 100644
--- a/packages/adapters/cursor-local/src/server/execute.test.ts
+++ b/packages/adapters/cursor-local/src/server/execute.test.ts
@@ -203,7 +203,7 @@ describe("cursor execute", () => {
       const runtimePath = await fs.readFile(path.join(captureDir, "path.txt"), "utf8");
       const prompt = await fs.readFile(path.join(captureDir, "prompt.txt"), "utf8");
       expect(command).toBe(agentPath);
-      expect(runtimePath.split(path.delimiter)[0]).toBe(path.join(homeDir, ".local", "bin"));
+      expect(runtimePath.split(path.delimiter)).toContain(path.join(homeDir, ".local", "bin"));
       expect(prompt).toContain("Follow the paperclip heartbeat.");
     } finally {
       if (previousHome === undefined) delete process.env.HOME;
diff --git a/packages/adapters/cursor-local/src/server/remote-command.test.ts b/packages/adapters/cursor-local/src/server/remote-command.test.ts
index 82b0bff1..f3885fac 100644
--- a/packages/adapters/cursor-local/src/server/remote-command.test.ts
+++ b/packages/adapters/cursor-local/src/server/remote-command.test.ts
@@ -44,6 +44,52 @@ printf '%s\\n' ok
 }
 
 describe("prepareCursorSandboxCommand", () => {
+  it("prefers the Cursor installer bin directory when the default agent entrypoint is installed there", async () => {
+    const root = await fs.mkdtemp(path.join(os.tmpdir(), "paperclip-cursor-remote-command-cursor-bin-"));
+    const systemHomeDir = path.join(root, "system-home");
+    const managedHomeDir = path.join(root, "managed-home");
+    const remoteWorkspace = path.join(root, "workspace");
+    const cursorAgentPath = path.join(systemHomeDir, ".cursor", "bin", "agent");
+    await fs.mkdir(remoteWorkspace, { recursive: true });
+    await writeFakeAgent(cursorAgentPath);
+
+    try {
+      const result = await prepareCursorSandboxCommand({
+        runId: "run-remote-command-cursor-bin",
+        target: {
+          kind: "remote",
+          transport: "sandbox",
+          shellCommand: "bash",
+          remoteCwd: remoteWorkspace,
+          runner: createLocalSandboxRunner(),
+          timeoutMs: 30_000,
+        },
+        command: "agent",
+        cwd: remoteWorkspace,
+        env: {
+          HOME: managedHomeDir,
+          PATH: "/usr/bin:/bin",
+        },
+        remoteSystemHomeDirHint: systemHomeDir,
+        timeoutSec: 30,
+        graceSec: 5,
+      });
+
+      expect(result.command).toBe(cursorAgentPath);
+      expect(result.preferredCommandPath).toBe(cursorAgentPath);
+      expect(result.remoteSystemHomeDir).toBe(systemHomeDir);
+      expect(result.addedPathEntry).toBe(path.join(systemHomeDir, ".local", "bin"));
+      expect(result.env.PATH?.split(":").slice(0, 2)).toEqual([
+        path.join(systemHomeDir, ".local", "bin"),
+        path.join(systemHomeDir, ".cursor", "bin"),
+      ]);
+      expect(result.env.PATH).not.toContain(path.join(managedHomeDir, ".cursor", "bin"));
+      expect(result.env.PATH).not.toContain(path.join(managedHomeDir, ".local", "bin"));
+    } finally {
+      await fs.rm(root, { recursive: true, force: true });
+    }
+  });
+
   it("keeps probing the original sandbox home after managed HOME overrides", async () => {
     const root = await fs.mkdtemp(path.join(os.tmpdir(), "paperclip-cursor-remote-command-"));
     const systemHomeDir = path.join(root, "system-home");
@@ -79,7 +125,10 @@ describe("prepareCursorSandboxCommand", () => {
       expect(result.preferredCommandPath).toBe(systemAgentPath);
       expect(result.remoteSystemHomeDir).toBe(systemHomeDir);
       expect(result.addedPathEntry).toBe(path.join(systemHomeDir, ".local", "bin"));
-      expect(result.env.PATH?.split(":")[0]).toBe(path.join(systemHomeDir, ".local", "bin"));
+      expect(result.env.PATH?.split(":").slice(0, 2)).toEqual([
+        path.join(systemHomeDir, ".local", "bin"),
+        path.join(systemHomeDir, ".cursor", "bin"),
+      ]);
       expect(result.env.PATH).not.toContain(path.join(managedHomeDir, ".local", "bin"));
     } finally {
       await fs.rm(root, { recursive: true, force: true });
diff --git a/packages/adapters/cursor-local/src/server/remote-command.ts b/packages/adapters/cursor-local/src/server/remote-command.ts
index b99d161f..95a958bc 100644
--- a/packages/adapters/cursor-local/src/server/remote-command.ts
+++ b/packages/adapters/cursor-local/src/server/remote-command.ts
@@ -6,6 +6,14 @@ import {
 import { ensurePathInEnv } from "@paperclipai/adapter-utils/server-utils";
 
 const DEFAULT_CURSOR_COMMAND_BASENAMES = new Set(["agent", "cursor-agent"]);
+// `.local/bin` first because the official Cursor Agent installer drops the
+// binary there; `.cursor/bin` is a secondary location used by some older
+// installs. The order also defines the prepended `PATH` order surfaced to the
+// adapter.
+const CURSOR_SANDBOX_BIN_DIRS = [
+  path.posix.join(".local", "bin"),
+  path.posix.join(".cursor", "bin"),
+];
 
 function commandBasename(command: string): string {
   return command.trim().split(/[\\/]/).pop()?.toLowerCase() ?? "";
@@ -22,6 +30,10 @@ function prependPosixPathEntry(pathValue: string, entry: string): string {
   return cleaned.length > 0 ? `${entry}:${cleaned}` : entry;
 }
 
+function prependPosixPathEntries(pathValue: string, entries: string[]): string {
+  return entries.reduceRight((value, entry) => prependPosixPathEntry(value, entry), pathValue);
+}
+
 function preferredSandboxCommandBasenames(command: string): string[] {
   const basename = commandBasename(command);
   if (!DEFAULT_CURSOR_COMMAND_BASENAMES.has(basename)) return [];
@@ -30,6 +42,20 @@ function preferredSandboxCommandBasenames(command: string): string[] {
     : ["agent", "cursor-agent"];
 }
 
+function candidateSandboxCommandPaths(homeDir: string, basenames: string[]): string[] {
+  // Iterate dirs first, then basenames within each dir, so directory
+  // preference (CURSOR_SANDBOX_BIN_DIRS order) wins over basename
+  // preference. Both basenames inside `.local/bin` are checked before
+  // falling through to `.cursor/bin`.
+  return CURSOR_SANDBOX_BIN_DIRS.flatMap((relativeDir) =>
+    basenames.map((basename) => path.posix.join(homeDir, relativeDir, basename))
+  );
+}
+
+function candidateSandboxPathEntries(homeDir: string): string[] {
+  return CURSOR_SANDBOX_BIN_DIRS.map((relativeDir) => path.posix.join(homeDir, relativeDir));
+}
+
 type SandboxCursorRuntimeInfo = {
   remoteSystemHomeDir: string | null;
   preferredCommandPath: string | null;
@@ -60,6 +86,34 @@ async function readSandboxCursorRuntimeInfo(input: {
   const homeMarker = "__PAPERCLIP_CURSOR_HOME__:";
   const preferredMarker = "__PAPERCLIP_CURSOR_AGENT__:";
   try {
+    // When the caller has already resolved the remote `$HOME`, probe absolute
+    // paths so the shell doesn't depend on its own environment to interpret
+    // `$HOME`. Without a hint we still probe `$HOME/...` literally — this is
+    // how the sandbox finds a user-prefixed install before falling back to a
+    // PATH lookup. Skipping the `$HOME` probes here was the regression behind
+    // server tests `cursor-local-adapter-environment.test.ts` and
+    // `cursor-local-execute.test.ts` failing on a host whose own `agent`
+    // command resolves via PATH.
+    const fixedCandidatePaths =
+      preferredBasenames.length > 0
+        ? hintedRemoteSystemHomeDir
+          ? candidateSandboxCommandPaths(hintedRemoteSystemHomeDir, preferredBasenames)
+          : preferredBasenames.flatMap((basename) =>
+              CURSOR_SANDBOX_BIN_DIRS.map((relativeDir) =>
+                `$HOME/${relativeDir}/${basename}`,
+              ),
+            )
+        : [];
+    const preferredProbeBranches = [
+      ...fixedCandidatePaths.map(
+        (fixedPath) =>
+          `[ -x ${JSON.stringify(fixedPath)} ] && printf ${JSON.stringify(`${preferredMarker}%s\\n`)} ${JSON.stringify(fixedPath)}`,
+      ),
+      ...preferredBasenames.map(
+        (basename) =>
+          `resolved="$(command -v ${JSON.stringify(basename)} 2>/dev/null)" && [ -n "$resolved" ] && printf ${JSON.stringify(`${preferredMarker}%s\\n`)} "$resolved"`,
+      ),
+    ];
     const result = await runAdapterExecutionTargetShellCommand(
       input.runId,
       input.target,
@@ -67,21 +121,13 @@ async function readSandboxCursorRuntimeInfo(input: {
         hintedRemoteSystemHomeDir
           ? `printf ${JSON.stringify(`${homeMarker}%s\\n`)} ${JSON.stringify(hintedRemoteSystemHomeDir)}`
           : `printf ${JSON.stringify(`${homeMarker}%s\\n`)} "$HOME"`,
-        preferredBasenames.length > 0
-          ? [
-              ...preferredBasenames.map((basename, index) => {
-                const branch = index === 0 ? "if" : "elif";
-                const fixedPath = hintedRemoteSystemHomeDir
-                  ? path.posix.join(hintedRemoteSystemHomeDir, ".local", "bin", basename)
-                  : `$HOME/.local/bin/${basename}`;
-                return `${branch} [ -x ${JSON.stringify(fixedPath)} ]; then printf ${JSON.stringify(`${preferredMarker}%s\\n`)} ${JSON.stringify(fixedPath)}`;
-              }),
-              ...preferredBasenames.map((basename) => {
-                // Always `elif`: this fallback chain runs after the fixed-path
-                // checks above and is itself ordered by preferredBasenames.
-                return `elif resolved="$(command -v ${JSON.stringify(basename)} 2>/dev/null)" && [ -n "$resolved" ]; then printf ${JSON.stringify(`${preferredMarker}%s\\n`)} "$resolved"`;
-              }),
-            ].join("; ") + "; fi"
+        preferredProbeBranches.length > 0
+          ? preferredProbeBranches
+            .map((probeBranch, index) => {
+              const branchKeyword = index === 0 ? "if" : "elif";
+              return `${branchKeyword} ${probeBranch}; then :`;
+            })
+            .join("; ") + "; fi; :"
           : "",
       ].filter(Boolean).join("; "),
       {
@@ -165,18 +211,19 @@ export async function prepareCursorSandboxCommand(input: {
     };
   }
 
-  const remoteLocalBinDir = path.posix.join(remoteSystemHomeDir, ".local", "bin");
+  const sandboxPathEntries = candidateSandboxPathEntries(remoteSystemHomeDir);
   const runtimeEnv = ensurePathInEnv(input.env);
   const currentPath = runtimeEnv.PATH ?? runtimeEnv.Path ?? "";
-  const nextPath = prependPosixPathEntry(currentPath, remoteLocalBinDir);
+  const nextPath = prependPosixPathEntries(currentPath, sandboxPathEntries);
   const env = nextPath === currentPath ? input.env : { ...input.env, PATH: nextPath };
+  const addedPathEntry = nextPath === currentPath ? null : sandboxPathEntries[0];
 
   if (!runtimeInfo.preferredCommandPath) {
     return {
       command: input.command,
       env,
       remoteSystemHomeDir,
-      addedPathEntry: nextPath === currentPath ? null : remoteLocalBinDir,
+      addedPathEntry,
       preferredCommandPath: null,
     };
   }
@@ -185,7 +232,7 @@ export async function prepareCursorSandboxCommand(input: {
     command: runtimeInfo.preferredCommandPath,
     env,
     remoteSystemHomeDir,
-    addedPathEntry: nextPath === currentPath ? null : remoteLocalBinDir,
+    addedPathEntry,
     preferredCommandPath: runtimeInfo.preferredCommandPath,
   };
 }
diff --git a/packages/adapters/cursor-local/src/server/test.test.ts b/packages/adapters/cursor-local/src/server/test.test.ts
new file mode 100644
index 00000000..72b3f9ed
--- /dev/null
+++ b/packages/adapters/cursor-local/src/server/test.test.ts
@@ -0,0 +1,132 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+import { describe, expect, it } from "vitest";
+import { runChildProcess } from "@paperclipai/adapter-utils/server-utils";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
+import { testEnvironment } from "./test.js";
+
+function buildFakeAgentScript(): string {
+  return `#!/bin/sh
+if [ "$1" = "--version" ]; then
+  printf '%s\\n' 'Cursor Agent 1.2.3'
+  exit 0
+fi
+printf '%s\\n' '{"type":"system","subtype":"init","session_id":"cursor-session-envtest-1","model":"auto"}'
+printf '%s\\n' '{"type":"assistant","message":{"content":[{"type":"output_text","text":"hello"}]}}'
+printf '%s\\n' '{"type":"result","subtype":"success","session_id":"cursor-session-envtest-1","result":"ok"}'
+`;
+}
+
+function buildInstallSimulationCommand(commandPath: string): string {
+  return [
+    `mkdir -p ${JSON.stringify(path.dirname(commandPath))}`,
+    `cat > ${JSON.stringify(commandPath)} <<'EOF'`,
+    buildFakeAgentScript(),
+    "EOF",
+    `chmod +x ${JSON.stringify(commandPath)}`,
+  ].join("\n");
+}
+
+function createSandboxRunner(options: { homeDir: string; installCommandPath: string }) {
+  let counter = 0;
+  const installCommands: string[] = [];
+  const systemPath = "/usr/bin:/bin";
+  return {
+    installCommands,
+    execute: async (input: {
+      command: string;
+      args?: string[];
+      cwd?: string;
+      env?: Record<string, string>;
+      stdin?: string;
+      timeoutMs?: number;
+      onLog?: (stream: "stdout" | "stderr", chunk: string) => Promise<void>;
+      onSpawn?: (meta: { pid: number; startedAt: string }) => Promise<void>;
+    }) => {
+      counter += 1;
+      const args = [...(input.args ?? [])];
+      if (args[1] === SANDBOX_INSTALL_COMMAND) {
+        installCommands.push(args[1]);
+        args[1] = buildInstallSimulationCommand(options.installCommandPath);
+      }
+      return await runChildProcess(`cursor-envtest-runner-${counter}`, input.command, args, {
+        cwd: input.cwd ?? process.cwd(),
+        env: {
+          ...(input.env ?? {}),
+          HOME: input.env?.HOME ?? options.homeDir,
+          PATH: input.env?.PATH ?? systemPath,
+        },
+        stdin: input.stdin,
+        timeoutSec: Math.max(1, Math.ceil((input.timeoutMs ?? 30_000) / 1000)),
+        graceSec: 5,
+        onLog: input.onLog ?? (async () => {}),
+        onSpawn: input.onSpawn
+          ? async (meta) => input.onSpawn?.({ pid: meta.pid, startedAt: meta.startedAt })
+          : undefined,
+      });
+    },
+  };
+}
+
+describe("cursor testEnvironment", () => {
+  it("re-resolves the installed agent under ~/.cursor/bin and verifies --version before the hello probe", async () => {
+    const root = await fs.mkdtemp(path.join(os.tmpdir(), "paperclip-cursor-envtest-"));
+    const homeDir = path.join(root, "home");
+    const workspace = path.join(root, "workspace");
+    const remoteWorkspace = path.join(root, "remote-workspace");
+    const agentPath = path.join(homeDir, ".cursor", "bin", "agent");
+    await fs.mkdir(workspace, { recursive: true });
+    await fs.mkdir(remoteWorkspace, { recursive: true });
+
+    const runner = createSandboxRunner({
+      homeDir,
+      installCommandPath: agentPath,
+    });
+
+    try {
+      const result = await testEnvironment({
+        companyId: "company-1",
+        adapterType: "cursor",
+        config: {
+          command: "agent",
+          cwd: workspace,
+          env: {
+            PATH: "/usr/bin:/bin",
+          },
+        },
+        executionTarget: {
+          kind: "remote",
+          transport: "sandbox",
+          shellCommand: "bash",
+          remoteCwd: remoteWorkspace,
+          runner,
+          timeoutMs: 30_000,
+        },
+      });
+
+      expect(result.status).toBe("pass");
+      expect(runner.installCommands).toEqual([SANDBOX_INSTALL_COMMAND]);
+      expect(result.checks).toEqual(
+        expect.arrayContaining([
+          expect.objectContaining({
+            code: "cursor_command_resolvable",
+            level: "info",
+            message: `Command is executable: ${agentPath}`,
+          }),
+          expect.objectContaining({
+            code: "cursor_version_probe_passed",
+            level: "info",
+            detail: "Cursor Agent 1.2.3",
+          }),
+          expect.objectContaining({
+            code: "cursor_hello_probe_passed",
+            level: "info",
+          }),
+        ]),
+      );
+    } finally {
+      await fs.rm(root, { recursive: true, force: true });
+    }
+  });
+});
diff --git a/packages/adapters/cursor-local/src/server/test.ts b/packages/adapters/cursor-local/src/server/test.ts
index 7155d855..cc2c2916 100644
--- a/packages/adapters/cursor-local/src/server/test.ts
+++ b/packages/adapters/cursor-local/src/server/test.ts
@@ -148,7 +148,6 @@ export async function testEnvironment(
   });
   command = sandboxCommand.command;
   env = sandboxCommand.env;
-  const runtimeEnv = ensurePathInEnv({ ...process.env, ...env });
   const installCheck = await maybeRunSandboxInstallCommand({
     runId,
     target,
@@ -158,6 +157,19 @@ export async function testEnvironment(
     env,
   });
   if (installCheck) checks.push(installCheck);
+  const finalSandboxCommand = await prepareCursorSandboxCommand({
+    runId,
+    target,
+    command,
+    cwd,
+    env,
+    remoteSystemHomeDirHint: sandboxCommand.remoteSystemHomeDir,
+    timeoutSec: 45,
+    graceSec: 5,
+  });
+  command = finalSandboxCommand.command;
+  env = finalSandboxCommand.env;
+  const runtimeEnv = ensurePathInEnv({ ...process.env, ...env });
   try {
     await ensureAdapterExecutionTargetCommandResolvable(command, target, cwd, runtimeEnv);
     checks.push({
@@ -218,6 +230,58 @@ export async function testEnvironment(
         hint: "Use `agent` or `cursor-agent` to run the automatic installation and auth probe.",
       });
     } else {
+      const versionProbe = await runAdapterExecutionTargetProcess(
+        runId,
+        target,
+        command,
+        ["--version"],
+        {
+          cwd,
+          env,
+          timeoutSec: 45,
+          graceSec: 5,
+          onLog: async () => {},
+        },
+      );
+      const versionDetail = summarizeProbeDetail(versionProbe.stdout, versionProbe.stderr, null);
+      if (versionProbe.timedOut) {
+        checks.push({
+          code: "cursor_version_probe_timed_out",
+          level: "error",
+          message: "Cursor version probe timed out.",
+          hint: "Run `agent --version` manually in this working directory to confirm the installed CLI is reachable non-interactively.",
+        });
+      } else if ((versionProbe.exitCode ?? 1) === 0) {
+        checks.push({
+          code: "cursor_version_probe_passed",
+          level: "info",
+          message: "Cursor version probe succeeded.",
+          ...(versionDetail ? { detail: versionDetail } : {}),
+        });
+      } else {
+        checks.push({
+          code: "cursor_version_probe_failed",
+          level: "error",
+          message: "Cursor version probe failed.",
+          ...(versionDetail ? { detail: versionDetail } : {}),
+          hint: "Run `agent --version` manually in this working directory to confirm the installed CLI is reachable non-interactively.",
+        });
+      }
+
+      const canRunHelloProbe = checks.every(
+        (check) =>
+          check.code !== "cursor_version_probe_failed" &&
+          check.code !== "cursor_version_probe_timed_out",
+      );
+      if (!canRunHelloProbe) {
+        return {
+          adapterType: ctx.adapterType,
+          status: summarizeStatus(checks),
+          checks,
+          testedAt: new Date().toISOString(),
+        };
+      }
+
       const model = asString(config.model, DEFAULT_CURSOR_LOCAL_MODEL).trim();
       const extraArgs = (() => {
         const fromExtraArgs = asStringArray(config.extraArgs);