diff --git a/packages/adapters/cursor-local/src/index.ts b/packages/adapters/cursor-local/src/index.ts
index 5c4e2356..09d29db4 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 "~/.local/bin/cursor-agent" when the default Cursor entrypoint is requested, so standard E2B-style installs do not need hardcoded absolute command paths.
+- 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.
 `;
diff --git a/packages/adapters/cursor-local/src/server/execute.remote.test.ts b/packages/adapters/cursor-local/src/server/execute.remote.test.ts
index 66da89d4..0617aae3 100644
--- a/packages/adapters/cursor-local/src/server/execute.remote.test.ts
+++ b/packages/adapters/cursor-local/src/server/execute.remote.test.ts
@@ -103,6 +103,7 @@ describe("cursor remote execution", () => {
     await mkdir(workspaceDir, { recursive: true });
     await mkdir(alternateWorkspaceDir, { recursive: true });
 
+    const managedRemoteWorkspace = "/remote/workspace/.paperclip-runtime/runs/run-1/workspace";
     const result = await execute({
       runId: "run-1",
       agent: {
@@ -158,21 +159,19 @@ describe("cursor remote execution", () => {
 
     expect(result.sessionParams).toMatchObject({
       sessionId: "cursor-session-1",
-      cwd: "/remote/workspace",
+      cwd: managedRemoteWorkspace,
       remoteExecution: {
         transport: "ssh",
         host: "127.0.0.1",
         port: 2222,
         username: "fixture",
-        remoteCwd: "/remote/workspace",
+        remoteCwd: managedRemoteWorkspace,
       },
     });
     expect(prepareWorkspaceForSshExecution).toHaveBeenCalledTimes(1);
     expect(syncDirectoryToSsh).toHaveBeenCalledTimes(1);
     expect(syncDirectoryToSsh).toHaveBeenCalledWith(expect.objectContaining({
-      // Asset sync targets the per-run managed subdirectory even though the
-      // cursor adapter still runs commands from the workspace root.
-      remoteDir: "/remote/workspace/.paperclip-runtime/runs/run-1/workspace/.paperclip-runtime/cursor/skills",
+      remoteDir: `${managedRemoteWorkspace}/.paperclip-runtime/cursor/skills`,
       followSymlinks: true,
     }));
     expect(runSshCommand).toHaveBeenCalledWith(
@@ -184,12 +183,12 @@ describe("cursor remote execution", () => {
       | [string, string, string[], { env: Record<string, string>; remoteExecution?: { remoteCwd: string } | null }]
       | undefined;
     expect(call?.[2]).toContain("--workspace");
-    expect(call?.[2]).toContain("/remote/workspace");
-    expect(call?.[3].env.PAPERCLIP_WORKSPACE_CWD).toBe("/remote/workspace");
+    expect(call?.[2]).toContain(managedRemoteWorkspace);
+    expect(call?.[3].env.PAPERCLIP_WORKSPACE_CWD).toBe(managedRemoteWorkspace);
     expect(JSON.parse(call?.[3].env.PAPERCLIP_WORKSPACES_JSON ?? "[]")).toEqual([
       {
         workspaceId: "workspace-1",
-        cwd: "/remote/workspace",
+        cwd: managedRemoteWorkspace,
         repoUrl: "https://github.com/paperclipai/paperclip.git",
         repoRef: "main",
       },
@@ -201,7 +200,7 @@ describe("cursor remote execution", () => {
     ]);
     expect(call?.[3].env.PAPERCLIP_API_URL).toBe("http://127.0.0.1:4310");
     expect(call?.[3].env.PAPERCLIP_API_BRIDGE_MODE).toBe("queue_v1");
-    expect(call?.[3].remoteExecution?.remoteCwd).toBe("/remote/workspace");
+    expect(call?.[3].remoteExecution?.remoteCwd).toBe(managedRemoteWorkspace);
     expect(startAdapterExecutionTargetPaperclipBridge).toHaveBeenCalledTimes(1);
     expect(restoreWorkspaceFromSshExecution).toHaveBeenCalledTimes(1);
   });
@@ -212,6 +211,7 @@ describe("cursor remote execution", () => {
     const workspaceDir = path.join(rootDir, "workspace");
     await mkdir(workspaceDir, { recursive: true });
 
+    const managedRemoteWorkspace = "/remote/workspace/.paperclip-runtime/runs/run-ssh-resume/workspace";
     await execute({
       runId: "run-ssh-resume",
       agent: {
@@ -225,13 +225,13 @@ describe("cursor remote execution", () => {
         sessionId: "session-123",
         sessionParams: {
           sessionId: "session-123",
-          cwd: "/remote/workspace",
+          cwd: managedRemoteWorkspace,
           remoteExecution: {
             transport: "ssh",
             host: "127.0.0.1",
             port: 2222,
             username: "fixture",
-            remoteCwd: "/remote/workspace",
+            remoteCwd: managedRemoteWorkspace,
           },
         },
         sessionDisplayId: "session-123",
diff --git a/packages/adapters/cursor-local/src/server/execute.test.ts b/packages/adapters/cursor-local/src/server/execute.test.ts
new file mode 100644
index 00000000..d83101ab
--- /dev/null
+++ b/packages/adapters/cursor-local/src/server/execute.test.ts
@@ -0,0 +1,352 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+import { describe, expect, it, vi } from "vitest";
+import type { AdapterExecutionTarget } from "@paperclipai/adapter-utils/execution-target";
+import { runChildProcess } from "@paperclipai/adapter-utils/server-utils";
+import { SANDBOX_INSTALL_COMMAND } from "../index.js";
+import { execute } from "./execute.js";
+
+type PrepareCursorSandboxCommandInput = {
+  runId: string;
+  target: AdapterExecutionTarget | null | undefined;
+  command: string;
+  cwd: string;
+  env: Record<string, string>;
+  remoteSystemHomeDirHint?: string | null;
+  timeoutSec: number;
+  graceSec: number;
+};
+
+type PrepareCursorSandboxCommandResult = {
+  command: string;
+  env: Record<string, string>;
+  remoteSystemHomeDir: string | null;
+  addedPathEntry: string | null;
+  preferredCommandPath: string | null;
+};
+
+const {
+  setPrepareCursorSandboxCommand,
+} = vi.hoisted(() => {
+  const setPrepareCursorSandboxCommand = vi.fn<
+    (input: PrepareCursorSandboxCommandInput) => Promise<PrepareCursorSandboxCommandResult>
+  >();
+  return { setPrepareCursorSandboxCommand };
+});
+
+vi.mock("@paperclipai/adapter-utils/execution-target", async () => {
+  const actual = await vi.importActual<typeof import("@paperclipai/adapter-utils/execution-target")>(
+    "@paperclipai/adapter-utils/execution-target",
+  );
+  return {
+    ...actual,
+    startAdapterExecutionTargetPaperclipBridge: async () => null,
+  };
+});
+
+vi.mock("./remote-command.js", async () => {
+  const actual = await vi.importActual<typeof import("./remote-command.js")>("./remote-command.js");
+  return {
+    ...actual,
+    prepareCursorSandboxCommand: async (input: Parameters<typeof actual.prepareCursorSandboxCommand>[0]) => {
+      return setPrepareCursorSandboxCommand(input);
+    },
+  };
+});
+
+function buildFakeAgentScript(captureDir: string): string {
+  return `#!/bin/sh
+cat > ${JSON.stringify(path.join(captureDir, "prompt.txt"))}
+printf '%s' "$0" > ${JSON.stringify(path.join(captureDir, "command.txt"))}
+printf '%s' "$PATH" > ${JSON.stringify(path.join(captureDir, "path.txt"))}
+printf '%s\\n' '{"type":"system","subtype":"init","session_id":"cursor-session-fresh-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-fresh-1","result":"ok"}'
+`;
+}
+
+function buildInstallSimulationCommand(commandPath: string, captureDir: string): string {
+  return [
+    `mkdir -p ${JSON.stringify(path.dirname(commandPath))}`,
+    `mkdir -p ${JSON.stringify(captureDir)}`,
+    `cat > ${JSON.stringify(commandPath)} <<'EOF'`,
+    buildFakeAgentScript(captureDir),
+    "EOF",
+    `chmod +x ${JSON.stringify(commandPath)}`,
+  ].join("\n");
+}
+
+function createFreshLeaseSandboxRunner(options: {
+  homeDir: string;
+  installCommandPath: string;
+  captureDir: string;
+}) {
+  let counter = 0;
+  const installCommands: string[] = [];
+  const systemPath = [
+    "/usr/local/bin",
+    "/opt/homebrew/bin",
+    "/usr/local/sbin",
+    "/usr/bin",
+    "/bin",
+    "/usr/sbin",
+    "/sbin",
+  ].join(path.delimiter);
+
+  return {
+    installCommands,
+    execute: async (input: {
+      command: string;
+      args?: string[];
+      cwd?: string;
+      env?: Record<string, string>;
+      stdin?: string;
+      timeoutMs?: number;
+      onLog?: (stream: "stdout" | "stderr", chunk: string) => Promise<void>;
+      onSpawn?: (meta: { pid: number; startedAt: string }) => Promise<void>;
+    }) => {
+      counter += 1;
+      const args = [...(input.args ?? [])];
+      if (args[1] === SANDBOX_INSTALL_COMMAND) {
+        installCommands.push(args[1]);
+        args[1] = buildInstallSimulationCommand(options.installCommandPath, options.captureDir);
+      }
+
+      const inheritedPath = input.env?.PATH ?? systemPath;
+      const pathWithLocalBin = `${path.join(options.homeDir, ".local", "bin")}${path.delimiter}${inheritedPath}`;
+      const env = {
+        ...(input.env ?? {}),
+        HOME: input.env?.HOME ?? options.homeDir,
+        PATH: pathWithLocalBin,
+      };
+
+      return await runChildProcess(`cursor-fresh-lease-${counter}`, input.command, args, {
+        cwd: input.cwd ?? process.cwd(),
+        env,
+        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 execute", () => {
+  it("installs the default agent command on a fresh sandbox lease before execution", async () => {
+    setPrepareCursorSandboxCommand.mockReset();
+    setPrepareCursorSandboxCommand.mockImplementation(async (input) => {
+      const actual = await vi.importActual<typeof import("./remote-command.js")>("./remote-command.js");
+      return actual.prepareCursorSandboxCommand(input);
+    });
+
+    const root = await fs.mkdtemp(path.join(os.tmpdir(), "paperclip-cursor-fresh-lease-"));
+    const homeDir = path.join(root, "home");
+    const workspace = path.join(root, "workspace");
+    const remoteWorkspace = path.join(root, "remote-workspace");
+    const captureDir = path.join(root, "capture");
+    const agentPath = path.join(homeDir, ".local", "bin", "agent");
+    await fs.mkdir(workspace, { recursive: true });
+    await fs.mkdir(remoteWorkspace, { recursive: true });
+
+    const runner = createFreshLeaseSandboxRunner({
+      homeDir,
+      installCommandPath: agentPath,
+      captureDir,
+    });
+
+    const previousHome = process.env.HOME;
+    process.env.HOME = homeDir;
+
+    try {
+      const result = await execute({
+        runId: "run-fresh-lease-1",
+        agent: {
+          id: "agent-1",
+          companyId: "company-1",
+          name: "Cursor Coder",
+          adapterType: "cursor",
+          adapterConfig: {},
+        },
+        runtime: {
+          sessionId: null,
+          sessionParams: null,
+          sessionDisplayId: null,
+          taskKey: null,
+        },
+        executionTarget: {
+          kind: "remote",
+          transport: "sandbox",
+          remoteCwd: remoteWorkspace,
+          runner,
+          timeoutMs: 30_000,
+        },
+        config: {
+          command: "agent",
+          cwd: workspace,
+          promptTemplate: "Follow the paperclip heartbeat.",
+        },
+        context: {},
+        authToken: "run-jwt-token",
+        onLog: async () => {},
+      });
+
+      expect(result.exitCode).toBe(0);
+      expect(result.errorMessage).toBeNull();
+      expect(runner.installCommands).toEqual([SANDBOX_INSTALL_COMMAND]);
+
+      const command = await fs.readFile(path.join(captureDir, "command.txt"), "utf8");
+      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(prompt).toContain("Follow the paperclip heartbeat.");
+    } finally {
+      if (previousHome === undefined) delete process.env.HOME;
+      else process.env.HOME = previousHome;
+      await fs.rm(root, { recursive: true, force: true });
+    }
+  });
+
+  it("reruns sandbox command resolution after managed runtime setup and keeps the original sandbox home", async () => {
+    setPrepareCursorSandboxCommand.mockReset();
+    const prepareInputs: PrepareCursorSandboxCommandInput[] = [];
+    let finalPreparedCommand: string | null = null;
+
+    const rootDir = await fs.mkdtemp(path.join(os.tmpdir(), "paperclip-cursor-fresh-lease-managed-"));
+    const workspaceDir = path.join(rootDir, "workspace");
+    const remoteWorkspace = path.join(rootDir, "remote-workspace");
+    const systemHomeDir = path.join(rootDir, "system-home");
+    const managedCaptureDir = path.join(rootDir, "managed-capture");
+    await fs.mkdir(managedCaptureDir, { recursive: true });
+    await fs.mkdir(workspaceDir, { recursive: true });
+    await fs.mkdir(remoteWorkspace, { recursive: true });
+    const preferredAgentScript = `#!/bin/sh
+printf '%s\\n' '{"type":"system","subtype":"init","session_id":"cursor-session-fresh-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-fresh-1","result":"ok"}'
+`;
+
+    setPrepareCursorSandboxCommand.mockImplementation(async (input) => {
+      const call = prepareInputs.length;
+      prepareInputs.push(input);
+      if (call === 0) {
+        return {
+          command: input.command,
+          env: input.env,
+          remoteSystemHomeDir: systemHomeDir,
+          addedPathEntry: null,
+          preferredCommandPath: null,
+        };
+      }
+
+      expect(input.remoteSystemHomeDirHint).toBe(systemHomeDir);
+      const preferredCommandPath = path.join(systemHomeDir, ".local", "bin", input.command);
+      finalPreparedCommand = preferredCommandPath;
+      const runtimeEnv = {
+        ...input.env,
+        PATH: `${path.join(systemHomeDir, ".local", "bin")}${path.delimiter}${input.env.PATH}`,
+      };
+      await fs.mkdir(path.dirname(preferredCommandPath), { recursive: true });
+      await fs.writeFile(preferredCommandPath, preferredAgentScript);
+      await fs.chmod(preferredCommandPath, 0o755);
+      await fs.writeFile(path.join(managedCaptureDir, "agent-output.log"), preferredCommandPath);
+
+      return {
+        command: preferredCommandPath,
+        env: runtimeEnv,
+        remoteSystemHomeDir: systemHomeDir,
+        addedPathEntry: path.join(systemHomeDir, ".local", "bin"),
+        preferredCommandPath,
+      };
+    });
+
+    const runnerState = {
+      commands: [] as string[],
+    };
+    const runner = {
+      execute: async (input: { command: string; args?: string[]; env?: Record<string, string> }) => {
+        runnerState.commands.push(input.command);
+        if (input.command === "sh") {
+          return {
+            exitCode: 0,
+          signal: null,
+          timedOut: false,
+          stdout: "",
+          stderr: "",
+          pid: 555,
+          startedAt: new Date().toISOString(),
+        };
+        }
+
+        return runChildProcess(`cursor-fresh-lease-${runnerState.commands.length}`, input.command, input.args ?? [], {
+          cwd: remoteWorkspace,
+          env: input.env ?? {},
+          timeoutSec: 30,
+          graceSec: 5,
+          onLog: async () => {},
+          onSpawn: async () => {},
+        });
+      },
+    };
+
+    const runMeta: Array<{ command?: string; [key: string]: unknown }> = [];
+    const previousHome = process.env.HOME;
+    process.env.HOME = systemHomeDir;
+
+    try {
+      const command = "agent";
+      const result = await execute({
+        runId: "run-fresh-lease-managed",
+        agent: {
+          id: "agent-1",
+          companyId: "company-1",
+          name: "Cursor Coder",
+          adapterType: "cursor",
+          adapterConfig: {},
+        },
+        runtime: {
+          sessionId: null,
+          sessionParams: null,
+          sessionDisplayId: null,
+          taskKey: null,
+        },
+        executionTarget: {
+          kind: "remote",
+          transport: "sandbox",
+          remoteCwd: remoteWorkspace,
+          providerKey: "fixture",
+          runner: runner,
+          timeoutMs: 30_000,
+        },
+        config: {
+          command,
+          cwd: workspaceDir,
+          promptTemplate: "Run against runtime-managed command.",
+        },
+        context: {},
+        authToken: "run-jwt-token",
+        onLog: async () => {},
+        onMeta: async (meta) => {
+          runMeta.push(meta as unknown as { command?: string; [key: string]: unknown });
+        },
+      });
+
+      expect(result.exitCode).toBe(0);
+      expect(prepareInputs).toHaveLength(2);
+      expect(finalPreparedCommand).not.toBeNull();
+      expect(finalPreparedCommand).toMatch(/\.local\/(bin|sbin)\/agent$/);
+      const resolvedCommand = runMeta.find(Boolean)?.command as string | undefined;
+      expect(resolvedCommand).toMatch(/\.local\/bin\/agent$/);
+      expect(resolvedCommand).toContain(path.join(systemHomeDir, ".local", "bin", command));
+    } finally {
+      if (previousHome === undefined) delete process.env.HOME;
+      else process.env.HOME = previousHome;
+      await fs.rm(rootDir, { recursive: true, force: true });
+    }
+  });
+});
diff --git a/packages/adapters/cursor-local/src/server/execute.ts b/packages/adapters/cursor-local/src/server/execute.ts
index 27180aa8..d04cc73b 100644
--- a/packages/adapters/cursor-local/src/server/execute.ts
+++ b/packages/adapters/cursor-local/src/server/execute.ts
@@ -6,6 +6,7 @@ import { inferOpenAiCompatibleBiller, type AdapterExecutionContext, type Adapter
 import {
   adapterExecutionTargetIsRemote,
   adapterExecutionTargetRemoteCwd,
+  overrideAdapterExecutionTargetRemoteCwd,
   adapterExecutionTargetSessionIdentity,
   adapterExecutionTargetSessionMatches,
   adapterExecutionTargetUsesManagedHome,
@@ -26,19 +27,18 @@ import {
   asNumber,
   asStringArray,
   parseObject,
-  applyPaperclipWorkspaceEnv,
   buildPaperclipEnv,
   buildInvocationEnvForLogs,
   ensureAbsoluteDirectory,
   ensurePaperclipSkillSymlink,
   ensurePathInEnv,
+  refreshPaperclipWorkspaceEnvForExecution,
   readPaperclipRuntimeSkillEntries,
   readPaperclipIssueWorkModeFromContext,
   resolvePaperclipDesiredSkillNames,
   removeMaintainerOnlySkillSymlinks,
   renderTemplate,
   renderPaperclipWakePrompt,
-  shapePaperclipWorkspaceEnvForExecution,
   stringifyPaperclipWakePayload,
   DEFAULT_PAPERCLIP_AGENT_PROMPT_TEMPLATE,
   joinPromptSections,
@@ -224,13 +224,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
   const useConfiguredInsteadOfAgentHome = workspaceSource === "agent_home" && configuredCwd.length > 0;
   const effectiveWorkspaceCwd = useConfiguredInsteadOfAgentHome ? "" : workspaceCwd;
   const cwd = effectiveWorkspaceCwd || configuredCwd || process.cwd();
-  const effectiveExecutionCwd = adapterExecutionTargetRemoteCwd(executionTarget, cwd);
-  const shapedWorkspaceEnv = shapePaperclipWorkspaceEnvForExecution({
-    workspaceCwd: effectiveWorkspaceCwd,
-    workspaceHints,
-    executionTargetIsRemote,
-    executionCwd: effectiveExecutionCwd,
-  });
+  let effectiveExecutionCwd = adapterExecutionTargetRemoteCwd(executionTarget, cwd);
   await ensureAbsoluteDirectory(cwd, { createIfMissing: true });
   const cursorSkillEntries = await readPaperclipRuntimeSkillEntries(config, __moduleDir);
   const desiredCursorSkillNames = resolvePaperclipDesiredSkillNames(config, cursorSkillEntries);
@@ -294,20 +288,19 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
   if (wakePayloadJson) {
     env.PAPERCLIP_WAKE_PAYLOAD_JSON = wakePayloadJson;
   }
-  applyPaperclipWorkspaceEnv(env, {
-    workspaceCwd: shapedWorkspaceEnv.workspaceCwd,
+  refreshPaperclipWorkspaceEnvForExecution({
+    env,
+    envConfig,
+    workspaceCwd: effectiveWorkspaceCwd,
     workspaceSource,
     workspaceId,
     workspaceRepoUrl,
     workspaceRepoRef,
+    workspaceHints,
     agentHome,
+    executionTargetIsRemote,
+    executionCwd: effectiveExecutionCwd,
   });
-  if (shapedWorkspaceEnv.workspaceHints.length > 0) {
-    env.PAPERCLIP_WORKSPACES_JSON = JSON.stringify(shapedWorkspaceEnv.workspaceHints);
-  }
-  for (const [k, v] of Object.entries(envConfig)) {
-    if (typeof v === "string") env[k] = v;
-  }
   if (!hasExplicitApiKey && authToken) {
     env.PAPERCLIP_API_KEY = authToken;
   }
@@ -324,10 +317,11 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     graceSec,
     onLog,
   });
-  // Probe the sandbox before the managed-home override so we discover
-  // cursor-agent from the real system HOME (e.g. ~/.local/bin/cursor-agent).
-  // The managed HOME set later is for runtime isolation, not for finding the CLI.
-  const sandboxCommand = await prepareCursorSandboxCommand({
+  // Probe the sandbox before the managed-home override so we discover the
+  // installer-managed agent symlinks from the real system HOME (for example
+  // ~/.local/bin/agent). The managed HOME set later is for runtime isolation,
+  // not for finding the CLI.
+  const initialSandboxCommand = await prepareCursorSandboxCommand({
     runId,
     target: executionTarget,
     command,
@@ -336,22 +330,9 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
     timeoutSec,
     graceSec,
   });
-  command = sandboxCommand.command;
-  env = sandboxCommand.env;
-  const effectiveEnv = Object.fromEntries(
-    Object.entries({ ...process.env, ...env }).filter(
-      (entry): entry is [string, string] => typeof entry[1] === "string",
-    ),
-  );
-  const billingType = resolveCursorBillingType(effectiveEnv);
-  const runtimeEnv = ensurePathInEnv(effectiveEnv);
-  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv, { installCommand: SANDBOX_INSTALL_COMMAND });
-  const resolvedCommand = await resolveAdapterExecutionTargetCommandForLogs(command, executionTarget, cwd, runtimeEnv);
-  let loggedEnv = buildInvocationEnvForLogs(env, {
-    runtimeEnv,
-    includeRuntimeKeys: ["HOME"],
-    resolvedCommand,
-  });
+  const sandboxSystemHomeDir = initialSandboxCommand.remoteSystemHomeDir;
+  command = initialSandboxCommand.command;
+  env = initialSandboxCommand.env;
 
   const extraArgs = (() => {
     const fromExtraArgs = asStringArray(config.extraArgs);
@@ -385,6 +366,20 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
         }],
       });
       restoreRemoteWorkspace = () => preparedExecutionTargetRuntime.restoreWorkspace();
+      effectiveExecutionCwd = preparedExecutionTargetRuntime.workspaceRemoteDir ?? effectiveExecutionCwd;
+      refreshPaperclipWorkspaceEnvForExecution({
+        env,
+        envConfig,
+        workspaceCwd: effectiveWorkspaceCwd,
+        workspaceSource,
+        workspaceId,
+        workspaceRepoUrl,
+        workspaceRepoRef,
+        workspaceHints,
+        agentHome,
+        executionTargetIsRemote,
+        executionCwd: effectiveExecutionCwd,
+      });
       remoteRuntimeRootDir = preparedExecutionTargetRuntime.runtimeRootDir;
       const managedHome = adapterExecutionTargetUsesManagedHome(executionTarget);
       if (managedHome && preparedExecutionTargetRuntime.runtimeRootDir) {
@@ -416,10 +411,43 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
       throw error;
     }
   }
-  if (executionTargetIsRemote && adapterExecutionTargetUsesPaperclipBridge(executionTarget)) {
-    paperclipBridge = await startAdapterExecutionTargetPaperclipBridge({
+  const finalSandboxCommand = executionTarget?.kind === "remote" && executionTarget.transport === "sandbox"
+    ? await prepareCursorSandboxCommand({
       runId,
       target: executionTarget,
+      command,
+      cwd,
+      env,
+      remoteSystemHomeDirHint: sandboxSystemHomeDir,
+      timeoutSec,
+      graceSec,
+    })
+    : null;
+  if (finalSandboxCommand) {
+    command = finalSandboxCommand.command;
+    env = finalSandboxCommand.env;
+  }
+  const runtimeExecutionTarget = overrideAdapterExecutionTargetRemoteCwd(executionTarget, effectiveExecutionCwd);
+  const effectiveEnv = Object.fromEntries(
+    Object.entries({ ...process.env, ...env }).filter(
+      (entry): entry is [string, string] => typeof entry[1] === "string",
+    ),
+  );
+  const billingType = resolveCursorBillingType(effectiveEnv);
+  const runtimeEnv = ensurePathInEnv(effectiveEnv);
+  await ensureAdapterExecutionTargetCommandResolvable(command, executionTarget, cwd, runtimeEnv, {
+    installCommand: SANDBOX_INSTALL_COMMAND,
+  });
+  const resolvedCommand = await resolveAdapterExecutionTargetCommandForLogs(command, executionTarget, cwd, runtimeEnv);
+  let loggedEnv = buildInvocationEnvForLogs(env, {
+    runtimeEnv,
+    includeRuntimeKeys: ["HOME"],
+    resolvedCommand,
+  });
+  if (executionTargetIsRemote && adapterExecutionTargetUsesPaperclipBridge(runtimeExecutionTarget)) {
+    paperclipBridge = await startAdapterExecutionTargetPaperclipBridge({
+      runId,
+      target: runtimeExecutionTarget,
       runtimeRootDir: remoteRuntimeRootDir,
       adapterKey: "cursor",
       hostApiToken: env.PAPERCLIP_API_KEY,
@@ -442,7 +470,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
   const canResumeSession =
     runtimeSessionId.length > 0 &&
     (runtimeSessionCwd.length === 0 || path.resolve(runtimeSessionCwd) === path.resolve(effectiveExecutionCwd)) &&
-    adapterExecutionTargetSessionMatches(runtimeRemoteExecution, executionTarget);
+    adapterExecutionTargetSessionMatches(runtimeRemoteExecution, runtimeExecutionTarget);
   const sessionId = canResumeSession ? runtimeSessionId : null;
   if (executionTargetIsRemote && runtimeSessionId && !canResumeSession) {
     await onLog(
@@ -482,11 +510,14 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
       notes.push("Auto-added --yolo to bypass interactive prompts.");
     }
     notes.push("Prompt is piped to Cursor via stdin.");
-    if (sandboxCommand.addedPathEntry) {
+    const sandboxCommand = finalSandboxCommand ?? initialSandboxCommand;
+    if (sandboxCommand?.addedPathEntry) {
       notes.push(`Remote sandbox runs prepend ${sandboxCommand.addedPathEntry} to PATH.`);
     }
-    if (sandboxCommand.preferredCommandPath) {
-      notes.push(`Remote sandbox runs prefer ${sandboxCommand.preferredCommandPath} when using the default Cursor entrypoint.`);
+    if (sandboxCommand?.preferredCommandPath) {
+      notes.push(
+        `Remote sandbox runs prefer ${sandboxCommand.preferredCommandPath} when using the default Cursor entrypoint.`,
+      );
     }
     if (!instructionsFilePath) return notes;
     if (instructionsPrefix.length > 0) {
@@ -589,7 +620,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
       }
     };
 
-    const proc = await runAdapterExecutionTargetProcess(runId, executionTarget, command, args, {
+    const proc = await runAdapterExecutionTargetProcess(runId, runtimeExecutionTarget, command, args, {
       cwd,
       env,
       timeoutSec,
@@ -647,7 +678,7 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
           ...(workspaceRepoRef ? { repoRef: workspaceRepoRef } : {}),
           ...(executionTargetIsRemote
             ? {
-                remoteExecution: adapterExecutionTargetSessionIdentity(executionTarget),
+                remoteExecution: adapterExecutionTargetSessionIdentity(runtimeExecutionTarget),
               }
             : {}),
         } as Record<string, unknown>)
diff --git a/packages/adapters/cursor-local/src/server/remote-command.test.ts b/packages/adapters/cursor-local/src/server/remote-command.test.ts
new file mode 100644
index 00000000..82b0bff1
--- /dev/null
+++ b/packages/adapters/cursor-local/src/server/remote-command.test.ts
@@ -0,0 +1,88 @@
+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 { prepareCursorSandboxCommand } from "./remote-command.js";
+
+function createLocalSandboxRunner() {
+  let counter = 0;
+  return {
+    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;
+      return await runChildProcess(`cursor-remote-command-${counter}`, input.command, input.args ?? [], {
+        cwd: input.cwd ?? process.cwd(),
+        env: input.env ?? {},
+        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,
+      });
+    },
+  };
+}
+
+async function writeFakeAgent(commandPath: string): Promise<void> {
+  const script = `#!/bin/sh
+printf '%s\\n' ok
+`;
+  await fs.mkdir(path.dirname(commandPath), { recursive: true });
+  await fs.writeFile(commandPath, script, "utf8");
+  await fs.chmod(commandPath, 0o755);
+}
+
+describe("prepareCursorSandboxCommand", () => {
+  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");
+    const managedHomeDir = path.join(root, "managed-home");
+    const remoteWorkspace = path.join(root, "workspace");
+    const systemAgentPath = path.join(systemHomeDir, ".local", "bin", "agent");
+    await fs.mkdir(remoteWorkspace, { recursive: true });
+    await writeFakeAgent(systemAgentPath);
+
+    try {
+      const result = await prepareCursorSandboxCommand({
+        runId: "run-remote-command-1",
+        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(systemAgentPath);
+      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).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 1edd6df0..b99d161f 100644
--- a/packages/adapters/cursor-local/src/server/remote-command.ts
+++ b/packages/adapters/cursor-local/src/server/remote-command.ts
@@ -22,6 +22,14 @@ function prependPosixPathEntry(pathValue: string, entry: string): string {
   return cleaned.length > 0 ? `${entry}:${cleaned}` : entry;
 }
 
+function preferredSandboxCommandBasenames(command: string): string[] {
+  const basename = commandBasename(command);
+  if (!DEFAULT_CURSOR_COMMAND_BASENAMES.has(basename)) return [];
+  return basename === "cursor-agent"
+    ? ["cursor-agent", "agent"]
+    : ["agent", "cursor-agent"];
+}
+
 type SandboxCursorRuntimeInfo = {
   remoteSystemHomeDir: string | null;
   preferredCommandPath: string | null;
@@ -40,10 +48,15 @@ async function readSandboxCursorRuntimeInfo(input: {
   command: string;
   cwd: string;
   env: Record<string, string>;
+  remoteSystemHomeDirHint?: string | null;
   timeoutSec: number;
   graceSec: number;
 }): Promise<SandboxCursorRuntimeInfo> {
-  const shouldCheckPreferredCommand = isDefaultCursorCommand(input.command) && !hasPathSeparator(input.command);
+  const preferredBasenames =
+    !hasPathSeparator(input.command)
+      ? preferredSandboxCommandBasenames(input.command)
+      : [];
+  const hintedRemoteSystemHomeDir = input.remoteSystemHomeDirHint?.trim() || null;
   const homeMarker = "__PAPERCLIP_CURSOR_HOME__:";
   const preferredMarker = "__PAPERCLIP_CURSOR_AGENT__:";
   try {
@@ -51,9 +64,24 @@ async function readSandboxCursorRuntimeInfo(input: {
       input.runId,
       input.target,
       [
-        `printf ${JSON.stringify(`${homeMarker}%s\\n`)} "$HOME"`,
-        shouldCheckPreferredCommand
-          ? `if [ -x "$HOME/.local/bin/cursor-agent" ]; then printf ${JSON.stringify(`${preferredMarker}%s\\n`)} "$HOME/.local/bin/cursor-agent"; fi`
+        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"
           : "",
       ].filter(Boolean).join("; "),
       {
@@ -100,6 +128,7 @@ export async function prepareCursorSandboxCommand(input: {
   command: string;
   cwd: string;
   env: Record<string, string>;
+  remoteSystemHomeDirHint?: string | null;
   timeoutSec: number;
   graceSec: number;
 }): Promise<PreparedCursorSandboxCommand> {
@@ -119,10 +148,12 @@ export async function prepareCursorSandboxCommand(input: {
     command: input.command,
     cwd: input.cwd,
     env: input.env,
+    remoteSystemHomeDirHint: input.remoteSystemHomeDirHint,
     timeoutSec: input.timeoutSec,
     graceSec: input.graceSec,
   });
-  const remoteSystemHomeDir = runtimeInfo.remoteSystemHomeDir;
+  const remoteSystemHomeDir =
+    runtimeInfo.remoteSystemHomeDir ?? input.remoteSystemHomeDirHint?.trim() ?? null;
 
   if (!remoteSystemHomeDir) {
     return {