@clipboard-health/groundcrew 1.10.1 → 1.11.0

package/README.md

@@ -81,6 +81,7 @@ This installs the `crew` binary. `@clipboard-health/clearance` is pulled in tran
      --claude \
      --codex \
      --copy-local-codex-auth \
+     --datadog \
      --github \
      --git-name "Your Name" \
      --git-email "you@users.noreply.github.com" \
@@ -89,7 +90,7 @@ This installs the `crew` binary. `@clipboard-health/clearance` is pulled in tran
      --checkpoint
    ```
 
-   Known MCP aliases are `linear`, `slack`, and `notion`. For another HTTP MCP server, pass `--mcp name=https://example.com/mcp`. The command creates the remote runner if needed, prepares `~/dev`, configures Git, runs selected auth flows, adds selected MCP servers to Claude Code, and then opens Claude so you can run `/mcp` and authenticate only those selected servers. With the Sprite provider, `--copy-local-codex-auth` copies `${CODEX_HOME:-$HOME/.codex}/auth.json` into `/home/sprite/.codex/auth.json` and then verifies `codex login status`; it never prints the file contents. Use `--skip-mcp-auth` when you only want to add MCP definitions, and run the `/mcp` step later.
+   Known MCP aliases are `linear`, `slack`, and `notion`. For another HTTP MCP server, pass `--mcp name=https://example.com/mcp`. The command creates the remote runner if needed, prepares `~/dev`, configures Git, runs selected auth flows, adds selected MCP servers to Claude Code, and then opens Claude so you can run `/mcp` and authenticate only those selected servers. With the Sprite provider, `--copy-local-codex-auth` copies `${CODEX_HOME:-$HOME/.codex}/auth.json` into `/home/sprite/.codex/auth.json` and then verifies `codex login status`; it never prints the file contents. `--datadog` installs a pinned `pup` release in the remote runner, verifies its checksum, installs the `dd-pup` guidance for Claude and Codex, verifies `pup auth status`, and when auth is missing temporarily runs `sprite proxy` for the OAuth callback while `pup auth login --read-only` runs in the remote runner. Open the Datadog URL printed by `pup` if your terminal does not open it automatically. Use `--skip-mcp-auth` when you only want to add MCP definitions, and run the `/mcp` step later.
 
    Repo setup is separate from runner setup and should run after the ticket branch exists, immediately before launching an agent. It clones/fetches the repo in the remote runner, checks out the requested branch (creating it from the base branch when it does not exist on origin), forwards only build-time secrets for the dependency install, removes the temporary secret file, clears those env vars, and then exits. It uses groundcrew's remote setup command.
 
@@ -180,7 +181,7 @@ Rules:
 ## Manual commands
 
 ```bash
-crew remote setup crew-claude-1 --claude --codex --copy-local-codex-auth --github --mcp linear --checkpoint
+crew remote setup crew-claude-1 --claude --codex --copy-local-codex-auth --datadog --github --mcp linear --checkpoint
 crew remote bootstrap crew-claude-1 core-utils --branch rocky-team-123
 crew remote sessions
 crew remote attach <session-id-or-command> --runner crew-claude-1

package/dist/cli.js

@@ -62,7 +62,7 @@ const SUBCOMMANDS = {
     },
     remote: {
         summary: "Create, authenticate, bootstrap, and inspect a remote runner",
-        usage: "setup <runner-name> [--claude] [--github] [--mcp <alias|name=url>] [--checkpoint]\n" +
+        usage: "setup <runner-name> [--claude] [--codex] [--datadog] [--github] [--mcp <alias|name=url>] [--checkpoint]\n" +
             "           → crew remote bootstrap <runner-name> <repo> [--branch <branch>]\n" +
             "           → crew remote sessions [<runner-name>]\n" +
             "           → crew remote attach <session-id-or-command> [--runner <runner-name>]\n" +

package/dist/commands/dispatcher.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"dispatcher.d.ts","sourceRoot":"","sources":["../../src/commands/dispatcher.ts"],"names":[],"mappings":"AAAA;;;;;;;GAOG;AAEH,OAAO,KAAK,EAAE,YAAY,EAAE,MAAM,aAAa,CAAC;AAEhD,OAAO,EAAE,KAAK,UAAU,EAA2C,MAAM,uBAAuB,CAAC;AACjG,OAAO,KAAK,EAAE,cAAc,EAAE,MAAM,kBAAkB,CAAC;AAEvD,OAAO,KAAK,EAAE,YAAY,EAAE,MAAM,iBAAiB,CAAC;AAGpD,OAAO,KAAK,EAAE,aAAa,EAAE,MAAM,qBAAqB,CAAC;AAczD,UAAU,cAAc;IACtB,MAAM,EAAE,cAAc,CAAC;IACvB,MAAM,EAAE,YAAY,CAAC;CACtB;AAED,MAAM,WAAW,UAAU;IACzB,OAAO,CAAC,UAAU,EAAE;QAClB,KAAK,EAAE,UAAU,CAAC;QAClB,eAAe,EAAE,SAAS,aAAa,EAAE,CAAC;QAC1C,+FAA+F;QAC/F,KAAK,EAAE,CAAC,MAAM,CAAC,EAAE,WAAW,KAAK,OAAO,CAAC,YAAY,CAAC,CAAC;QACvD,MAAM,EAAE,OAAO,CAAC;QAChB,MAAM,CAAC,EAAE,WAAW,CAAC;KACtB,GAAG,OAAO,CAAC,IAAI,CAAC,CAAC;CACnB;AAED,wBAAgB,gBAAgB,CAAC,IAAI,EAAE,cAAc,GAAG,UAAU,CAwNjE"}

package/dist/commands/dispatcher.js

@@ -6,7 +6,8 @@
  * Pure verdict logic lives in `eligibility.ts`; this module is responsible
  * for telemetry, Linear writes, and side-effecting setupWorkspace calls.
  */
-import { isGroundcrewIssue, } from "../lib/boardSource.js";
+import { isGroundcrewIssue } from "../lib/boardSource.js";
+import { createLinearIssueStatusUpdater } from "../lib/linearIssueStatus.js";
 import { errorMessage, log, logEvent } from "../lib/util.js";
 import { workspaces } from "../lib/workspaces.js";
 import { classifyBlockers, classifyEligibility, } from "./eligibility.js";
@@ -17,8 +18,7 @@ const MINUTES_PER_DAY = 24 * 60;
 const MINUTES_PER_WEEK = DAYS_PER_WEEK * MINUTES_PER_DAY;
 export function createDispatcher(deps) {
     const { config, client } = deps;
-    const inProgressStateByTeam = new Map();
-    let teamsMissingInProgress = new Set();
+    const issueStatusUpdater = createLinearIssueStatusUpdater({ config, client });
     function buildExhaustedSet(usage) {
         const exhausted = new Set();
         const sessionLimit = config.orchestrator.sessionLimitPercentage;
@@ -49,42 +49,6 @@ export function createDispatcher(deps) {
         }
         return exhausted;
     }
-    async function getInProgressStateId(teamId) {
-        if (teamId.length === 0) {
-            return undefined;
-        }
-        const cached = inProgressStateByTeam.get(teamId);
-        if (cached !== undefined) {
-            return cached;
-        }
-        // Negative cache is per-iteration so a team that's fixed in Linear during
-        // a `crew watch` session auto-recovers next tick. Within one iteration,
-        // every eligible ticket in a misconfigured team would otherwise re-fetch.
-        if (teamsMissingInProgress.has(teamId)) {
-            return undefined;
-        }
-        const team = await client.team(teamId);
-        const states = await team.states();
-        const inProgress = states.nodes.find((state) => state.name === config.linear.statuses.inProgress);
-        if (inProgress?.id === undefined) {
-            teamsMissingInProgress.add(teamId);
-            return undefined;
-        }
-        inProgressStateByTeam.set(teamId, inProgress.id);
-        return inProgress.id;
-    }
-    async function markInProgress(issue) {
-        const stateId = await getInProgressStateId(issue.teamId);
-        if (stateId === undefined) {
-            // Throw rather than log+return: if we silently swallowed this, the
-            // ticket would stay Todo forever while the workspace runs, which means
-            // every iteration re-enters the recovery path and the agent never
-            // counts toward maximumInProgress.
-            throw new Error(`Could not find "${config.linear.statuses.inProgress}" state for ${issue.id} (team ${issue.teamId.length > 0 ? issue.teamId : "?"}). Verify the status name in linear.statuses.inProgress matches the team's workflow.`);
-        }
-        await client.updateIssue(issue.uuid, { stateId });
-        log(`Marked ${issue.id} as ${config.linear.statuses.inProgress}`);
-    }
     function logSkip(verdict) {
         log(verdict.message);
         logEvent("dispatch", {
@@ -130,7 +94,7 @@ export function createDispatcher(deps) {
                     ? setupWorkspace(config, setupOptions)
                     : setupWorkspace(config, setupOptions, { signal }));
             }
-            await markInProgress(issue);
+            await issueStatusUpdater.markInProgress(issue);
             logEvent("dispatch", {
                 outcome: recovery ? "resumed" : "started",
                 ticket: issue.id,
@@ -153,7 +117,7 @@ export function createDispatcher(deps) {
     }
     async function runOnce(arguments_) {
         const { state, worktreeEntries, usage, dryRun, signal } = arguments_;
-        teamsMissingInProgress = new Set();
+        issueStatusUpdater.resetMissingInProgressCache();
         const activeCount = state.issues.filter((issue) => issue.status === config.linear.statuses.inProgress).length;
         const slots = config.orchestrator.maximumInProgress - activeCount;
         // Narrow Todo to tickets that opted in via an `agent-*` label.

package/dist/commands/remoteSetup.d.ts

@@ -8,6 +8,7 @@ export interface RemoteSetupOptions {
     shouldAuthenticateClaude: boolean;
     shouldAuthenticateCodex: boolean;
     shouldCopyLocalCodexAuth?: boolean;
+    shouldSetupDatadog?: boolean;
     shouldAuthenticateGithub: boolean;
     shouldAuthenticateMcp: boolean;
     shouldCheckpoint: boolean;

package/dist/commands/remoteSetup.d.ts.map

@@ -1 +1 @@
-{"version":3,"file":"remoteSetup.d.ts","sourceRoot":"","sources":["../../src/commands/remoteSetup.ts"],"names":[],"mappings":"AAwBA,MAAM,WAAW,SAAS;IACxB,IAAI,EAAE,MAAM,CAAC;IACb,GAAG,EAAE,MAAM,CAAC;CACb;AAED,MAAM,WAAW,kBAAkB;IACjC,UAAU,EAAE,MAAM,CAAC;IACnB,YAAY,EAAE,OAAO,CAAC;IACtB,wBAAwB,EAAE,OAAO,CAAC;IAClC,uBAAuB,EAAE,OAAO,CAAC;IACjC,wBAAwB,CAAC,EAAE,OAAO,CAAC;IACnC,wBAAwB,EAAE,OAAO,CAAC;IAClC,qBAAqB,EAAE,OAAO,CAAC;IAC/B,gBAAgB,EAAE,OAAO,CAAC;IAC1B,iBAAiB,EAAE,MAAM,CAAC;IAC1B,OAAO,CAAC,EAAE,MAAM,CAAC;IACjB,QAAQ,CAAC,EAAE,MAAM,CAAC;IAClB,UAAU,EAAE,SAAS,EAAE,CAAC;CACzB;AAED,MAAM,WAAW,sBAAsB;IACrC,UAAU,EAAE,MAAM,CAAC;IACnB,UAAU,EAAE,MAAM,CAAC;IACnB,KAAK,EAAE,MAAM,CAAC;IACd,UAAU,EAAE,MAAM,CAAC;IACnB,WAAW,EAAE,MAAM,EAAE,CAAC;IACtB,4BAA4B,EAAE,OAAO,CAAC;IACtC,gBAAgB,EAAE,OAAO,CAAC;IAC1B,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAED,MAAM,WAAW,qBAAqB;IACpC,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAED,MAAM,WAAW,mBAAmB;IAClC,MAAM,EAAE,MAAM,CAAC;IACf,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAED,MAAM,WAAW,oBAAoB;IACnC,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAED,MAAM,WAAW,sBAAsB;IACrC,cAAc,EAAE,MAAM,CAAC;IACvB,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AA4rBD,wBAAsB,yBAAyB,CAAC,OAAO,EAAE,sBAAsB,GAAG,OAAO,CAAC,IAAI,CAAC,CA6B9F;AAUD,wBAAsB,kBAAkB,CAAC,OAAO,EAAE,qBAAqB,GAAG,OAAO,CAAC,IAAI,CAAC,CAItF;AAED,wBAAsB,mBAAmB,CAAC,OAAO,EAAE,mBAAmB,GAAG,OAAO,CAAC,IAAI,CAAC,CAGrF;AAED,wBAAsB,mBAAmB,CAAC,OAAO,EAAE,oBAAoB,GAAG,OAAO,CAAC,IAAI,CAAC,CAItF;AAED,wBAAsB,2BAA2B,CAAC,OAAO,EAAE,sBAAsB,GAAG,OAAO,CAAC,IAAI,CAAC,CAGhG;AAYD,wBAAsB,iBAAiB,CAAC,OAAO,EAAE,kBAAkB,GAAG,OAAO,CAAC,IAAI,CAAC,CA6BlF;AAED,wBAAsB,SAAS,CAAC,IAAI,EAAE,MAAM,EAAE,GAAG,OAAO,CAAC,IAAI,CAAC,CA2B7D"}
+{"version":3,"file":"remoteSetup.d.ts","sourceRoot":"","sources":["../../src/commands/remoteSetup.ts"],"names":[],"mappings":"AAyBA,MAAM,WAAW,SAAS;IACxB,IAAI,EAAE,MAAM,CAAC;IACb,GAAG,EAAE,MAAM,CAAC;CACb;AAED,MAAM,WAAW,kBAAkB;IACjC,UAAU,EAAE,MAAM,CAAC;IACnB,YAAY,EAAE,OAAO,CAAC;IACtB,wBAAwB,EAAE,OAAO,CAAC;IAClC,uBAAuB,EAAE,OAAO,CAAC;IACjC,wBAAwB,CAAC,EAAE,OAAO,CAAC;IACnC,kBAAkB,CAAC,EAAE,OAAO,CAAC;IAC7B,wBAAwB,EAAE,OAAO,CAAC;IAClC,qBAAqB,EAAE,OAAO,CAAC;IAC/B,gBAAgB,EAAE,OAAO,CAAC;IAC1B,iBAAiB,EAAE,MAAM,CAAC;IAC1B,OAAO,CAAC,EAAE,MAAM,CAAC;IACjB,QAAQ,CAAC,EAAE,MAAM,CAAC;IAClB,UAAU,EAAE,SAAS,EAAE,CAAC;CACzB;AAED,MAAM,WAAW,sBAAsB;IACrC,UAAU,EAAE,MAAM,CAAC;IACnB,UAAU,EAAE,MAAM,CAAC;IACnB,KAAK,EAAE,MAAM,CAAC;IACd,UAAU,EAAE,MAAM,CAAC;IACnB,WAAW,EAAE,MAAM,EAAE,CAAC;IACtB,4BAA4B,EAAE,OAAO,CAAC;IACtC,gBAAgB,EAAE,OAAO,CAAC;IAC1B,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAED,MAAM,WAAW,qBAAqB;IACpC,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAED,MAAM,WAAW,mBAAmB;IAClC,MAAM,EAAE,MAAM,CAAC;IACf,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAED,MAAM,WAAW,oBAAoB;IACnC,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAED,MAAM,WAAW,sBAAsB;IACrC,cAAc,EAAE,MAAM,CAAC;IACvB,UAAU,CAAC,EAAE,MAAM,CAAC;CACrB;AAy0BD,wBAAsB,yBAAyB,CAAC,OAAO,EAAE,sBAAsB,GAAG,OAAO,CAAC,IAAI,CAAC,CA6B9F;AAUD,wBAAsB,kBAAkB,CAAC,OAAO,EAAE,qBAAqB,GAAG,OAAO,CAAC,IAAI,CAAC,CAItF;AAED,wBAAsB,mBAAmB,CAAC,OAAO,EAAE,mBAAmB,GAAG,OAAO,CAAC,IAAI,CAAC,CAGrF;AAED,wBAAsB,mBAAmB,CAAC,OAAO,EAAE,oBAAoB,GAAG,OAAO,CAAC,IAAI,CAAC,CAItF;AAED,wBAAsB,2BAA2B,CAAC,OAAO,EAAE,sBAAsB,GAAG,OAAO,CAAC,IAAI,CAAC,CAGhG;AAYD,wBAAsB,iBAAiB,CAAC,OAAO,EAAE,kBAAkB,GAAG,OAAO,CAAC,IAAI,CAAC,CAgClF;AAED,wBAAsB,SAAS,CAAC,IAAI,EAAE,MAAM,EAAE,GAAG,OAAO,CAAC,IAAI,CAAC,CA2B7D"}

package/dist/commands/remoteSetup.js

@@ -1,6 +1,7 @@
 import { existsSync, mkdtempSync, rmSync, writeFileSync } from "node:fs";
 import { homedir, tmpdir } from "node:os";
 import { join, resolve } from "node:path";
+import { setTimeout as sleep } from "node:timers/promises";
 import { BUILD_SECRET_NAMES, DEFAULT_REMOTE_SETUP_COMMAND, loadConfig, } from "../lib/config.js";
 import { shellSingleQuote } from "../lib/shell.js";
 import { getRemoteRunnerProvider, remoteConfigWithRunnerName, } from "../lib/spriteRemoteRunnerProvider.js";
@@ -14,6 +15,10 @@ const DEFAULT_CHECKPOINT_COMMENT = "groundcrew remote runner baseline: selected
 const CLAUDE_SUBSCRIPTION_LOGIN_FLAG = ["--claude", "ai"].join("");
 const DEFAULT_REPOSITORY_OWNER = "ClipboardHealth";
 const DEFAULT_BASE_BRANCH = "main";
+const DATADOG_PUP_VERSION = "0.63.0";
+const DATADOG_OAUTH_CALLBACK_PORT = 8000;
+const DATADOG_AUTH_STATUS_RETRY_ATTEMPTS = 5;
+const DATADOG_AUTH_STATUS_RETRY_DELAY_MS = 250;
 const REMOTE_SECRETS_FILE = "/tmp/groundcrew-build-secrets.env";
 const REMOTE_CODEX_AUTH_UPLOAD_FILE = "/tmp/groundcrew-codex-auth.json";
 const REMOTE_CODEX_AUTH_FILE = "/home/sprite/.codex/auth.json";
@@ -31,6 +36,7 @@ function usage() {
         "  --claude                    Authenticate Claude Code with a Claude subscription",
         "  --codex                     Authenticate Codex CLI",
         "  --copy-local-codex-auth     With --codex, copy local CODEX_HOME auth.json into the remote runner",
+        "  --datadog                   Install pup, add dd-pup skills, and authenticate Datadog",
         "  --github                    Authenticate gh for GitHub PRs",
         "  --mcp <alias|name=url>      Add/authenticate one MCP server; repeat for multiple",
         "                              Known aliases: linear, slack, notion",
@@ -134,6 +140,7 @@ function parseArguments(argv) {
     let shouldAuthenticateClaude = false;
     let shouldAuthenticateCodex = false;
     let shouldCopyLocalCodexAuth = false;
+    let shouldSetupDatadog = false;
     let shouldAuthenticateGithub = false;
     let shouldAuthenticateMcp = true;
     let shouldCheckpoint = false;
@@ -156,6 +163,10 @@ function parseArguments(argv) {
             shouldCopyLocalCodexAuth = true;
             continue;
         }
+        if (argument === "--datadog") {
+            shouldSetupDatadog = true;
+            continue;
+        }
         if (argument === "--github") {
             shouldAuthenticateGithub = true;
             continue;
@@ -202,6 +213,7 @@ function parseArguments(argv) {
         shouldAuthenticateClaude,
         shouldAuthenticateCodex,
         shouldCopyLocalCodexAuth,
+        shouldSetupDatadog,
         shouldAuthenticateGithub,
         shouldAuthenticateMcp,
         shouldCheckpoint,
@@ -457,6 +469,105 @@ async function authenticateCodex(arguments_) {
     }
     throw new Error("Codex login finished, but `codex login status` still reports not logged in inside the remote runner. Try `crew remote setup <runner-name> --codex --copy-local-codex-auth`.");
 }
+function datadogPupInstallCommand() {
+    const shellVariable = "$";
+    return [
+        "set -euo pipefail",
+        `version=${shellSingleQuote(DATADOG_PUP_VERSION)}`,
+        'case "$(uname -m)" in',
+        "  x86_64|amd64) arch=x86_64 ;;",
+        "  aarch64|arm64) arch=arm64 ;;",
+        '  *) echo "Unsupported Linux architecture: $(uname -m)" >&2; exit 1 ;;',
+        "esac",
+        `asset="pup_${shellVariable}{version}_Linux_${shellVariable}{arch}.tar.gz"`,
+        `base_url="https://github.com/DataDog/pup/releases/download/v${shellVariable}{version}"`,
+        'binary="$HOME/.local/bin/pup"',
+        'mkdir -p "$HOME/.local/bin"',
+        `if [ -x "$binary" ] && "$binary" version | grep -q "Pup ${shellVariable}{version} "; then "$binary" version; exit 0; fi`,
+        'install_dir="$(mktemp -d)"',
+        "trap 'rm -rf \"$install_dir\"' EXIT",
+        `archive="${shellVariable}{install_dir}/${shellVariable}{asset}"`,
+        `checksums="${shellVariable}{install_dir}/pup_${shellVariable}{version}_checksums.txt"`,
+        'curl -fsSL -o "$archive" "$base_url/$asset"',
+        `curl -fsSL -o "$checksums" "$base_url/pup_${shellVariable}{version}_checksums.txt"`,
+        `(cd "$install_dir" && grep " ${shellVariable}{asset}$" "$checksums" | sha256sum -c -)`,
+        'tar -xzf "$archive" -C "$HOME/.local/bin" pup',
+        'chmod 755 "$binary"',
+        '"$binary" version',
+    ].join("\n");
+}
+async function installDatadogPup(provider, config) {
+    log(`Installing Datadog pup ${DATADOG_PUP_VERSION} inside the remote runner`);
+    await provider.runCommand({
+        config,
+        remoteArguments: ["bash", "-lc", datadogPupInstallCommand()],
+    });
+}
+async function installDatadogPupSkills(provider, config) {
+    for (const platform of ["claude-code", "codex"]) {
+        // oxlint-disable-next-line no-await-in-loop -- installs are quick and ordered so logs stay readable.
+        await provider.runCommand({
+            config,
+            remoteArguments: ["pup", "skills", "install", platform, "--name", "dd-pup", "--yes"],
+        });
+    }
+}
+async function validateDatadogLogin(provider, config) {
+    return await commandSucceeds({
+        provider,
+        config,
+        remoteArguments: ["pup", "auth", "status"],
+    });
+}
+async function waitForDatadogLogin(provider, config) {
+    for (let attempt = 1; attempt <= DATADOG_AUTH_STATUS_RETRY_ATTEMPTS; attempt += 1) {
+        // oxlint-disable-next-line no-await-in-loop -- bounded polling smooths over Datadog OAuth propagation delay.
+        if (await validateDatadogLogin(provider, config)) {
+            return true;
+        }
+        if (attempt < DATADOG_AUTH_STATUS_RETRY_ATTEMPTS) {
+            // oxlint-disable-next-line no-await-in-loop -- retries are intentionally spaced.
+            await sleep(DATADOG_AUTH_STATUS_RETRY_DELAY_MS);
+        }
+    }
+    return false;
+}
+async function authenticateDatadog(provider, config) {
+    if (await validateDatadogLogin(provider, config)) {
+        return;
+    }
+    writeOutput();
+    writeOutput("Datadog OAuth will run inside the remote runner.");
+    writeOutput(`Groundcrew is forwarding local port ${DATADOG_OAUTH_CALLBACK_PORT} to the remote callback server while login runs.`);
+    writeOutput("Open the Datadog URL printed by pup if your terminal does not open it for you.");
+    writeOutput();
+    const proxy = await provider.startPortProxy(config, DATADOG_OAUTH_CALLBACK_PORT);
+    try {
+        await provider.runTtyCommand({
+            config,
+            remoteArguments: [
+                "pup",
+                "auth",
+                "login",
+                "--read-only",
+                "--callback-port",
+                String(DATADOG_OAUTH_CALLBACK_PORT),
+            ],
+        });
+    }
+    finally {
+        await proxy.close();
+    }
+    if (await waitForDatadogLogin(provider, config)) {
+        return;
+    }
+    throw new Error("Datadog auth finished, but `pup auth status` still reports not logged in inside the remote runner.");
+}
+async function setupDatadog(provider, config) {
+    await installDatadogPup(provider, config);
+    await installDatadogPupSkills(provider, config);
+    await authenticateDatadog(provider, config);
+}
 async function addMcpServer(arguments_) {
     const { provider, config, server } = arguments_;
     const exists = await commandSucceeds({
@@ -661,6 +772,9 @@ export async function setupRemoteRunner(options) {
             shouldCopyLocalAuth: options.shouldCopyLocalCodexAuth === true,
         });
     }
+    if (options.shouldSetupDatadog === true) {
+        await setupDatadog(provider, config);
+    }
     for (const server of options.mcpServers) {
         // oxlint-disable-next-line no-await-in-loop -- MCP additions are sequential so auth instructions stay ordered.
         await addMcpServer({ provider, config, server });

package/dist/commands/setupWorkspace.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"setupWorkspace.d.ts","sourceRoot":"","sources":["../../src/commands/setupWorkspace.ts"],"names":[],"mappings":"AAOA,OAAO,EAGL,KAAK,cAAc,EACnB,KAAK,eAAe,EACrB,MAAM,kBAAkB,CAAC;AAc1B,UAAU,aAAa;IACrB,KAAK,EAAE,MAAM,CAAC;IACd,WAAW,EAAE,MAAM,CAAC;CACrB;AAgBD,MAAM,WAAW,qBAAqB;IACpC,MAAM,EAAE,MAAM,CAAC;IACf,UAAU,EAAE,MAAM,CAAC;IACnB,KAAK,EAAE,MAAM,CAAC;IACd,MAAM,CAAC,EAAE,eAAe,CAAC;IACzB,wEAAwE;IACxE,OAAO,CAAC,EAAE,aAAa,CAAC;CACzB;AAED,MAAM,WAAW,wBAAwB;IACvC,MAAM,CAAC,EAAE,WAAW,CAAC;CACtB;AAsED,wBAAsB,cAAc,CAClC,MAAM,EAAE,cAAc,EACtB,OAAO,EAAE,qBAAqB,EAC9B,UAAU,GAAE,wBAA6B,GACxC,OAAO,CAAC,IAAI,CAAC,CA8Ef;AAuHD,wBAAsB,iBAAiB,CACrC,MAAM,EAAE,MAAM,EACd,OAAO,GAAE;IAAE,MAAM,CAAC,EAAE,OAAO,CAAA;CAAO,GACjC,OAAO,CAAC,IAAI,CAAC,CAyBf"}

package/dist/commands/setupWorkspace.js

@@ -6,6 +6,7 @@ import { fetchResolvedIssue } from "../lib/boardSource.js";
 import { BUILD_SECRET_NAMES, loadConfig, } from "../lib/config.js";
 import { detectHostCapabilities } from "../lib/host.js";
 import { buildLaunchCommand, buildRemoteLaunchCommand, shellSingleQuote, } from "../lib/launchCommand.js";
+import { createLinearIssueStatusUpdater } from "../lib/linearIssueStatus.js";
 import { assertLocalRunnerRequirements } from "../lib/localRunner.js";
 import { getRemoteRunnerProvider } from "../lib/spriteRemoteRunnerProvider.js";
 import { errorMessage, getLinearClient, log, readEnvironmentVariable } from "../lib/util.js";
@@ -245,4 +246,9 @@ export async function setupWorkspaceCli(ticket, options = {}) {
         runner: resolved.runner,
         details: { title: resolved.title, description: resolved.description },
     });
+    await createLinearIssueStatusUpdater({ config, client }).markInProgress({
+        id: ticket.toLowerCase(),
+        uuid: resolved.uuid,
+        teamId: resolved.teamId,
+    });
 }

package/dist/lib/boardSource.d.ts

@@ -65,11 +65,13 @@ interface BoardSourceDeps {
 export declare function createBoardSource(deps: BoardSourceDeps): BoardSource;
 export declare function isTerminalStatus(status: string, config: ResolvedConfig): boolean;
 interface ResolvedIssue {
+    uuid: string;
     title: string;
     description: string;
     repository: string;
     model: string;
     runner: WorkspaceRunner;
+    teamId: string;
 }
 /**
  * `agent-any` collapses to `models.default` here — manual setup doesn't run

package/dist/lib/boardSource.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"boardSource.d.ts","sourceRoot":"","sources":["../../src/lib/boardSource.ts"],"names":[],"mappings":"AAAA;;;;GAIG;AAEH,OAAO,KAAK,EAAE,YAAY,EAAE,MAAM,aAAa,CAAC;AAEhD,OAAO,EAGL,KAAK,cAAc,EACnB,KAAK,eAAe,EACrB,MAAM,aAAa,CAAC;AAMrB,MAAM,WAAW,OAAO;IACtB,EAAE,EAAE,MAAM,CAAC;IACX,KAAK,EAAE,MAAM,CAAC;IACd,MAAM,EAAE,MAAM,GAAG,SAAS,CAAC;CAC5B;AAED,MAAM,WAAW,KAAK;IACpB,EAAE,EAAE,MAAM,CAAC;IACX,IAAI,EAAE,MAAM,CAAC;IACb,KAAK,EAAE,MAAM,CAAC;IACd,MAAM,EAAE,MAAM,CAAC;IACf,QAAQ,EAAE,MAAM,CAAC;IACjB,QAAQ,EAAE,MAAM,CAAC;IACjB,SAAS,EAAE,MAAM,CAAC;IAClB,0FAA0F;IAC1F,UAAU,EAAE,MAAM,GAAG,SAAS,CAAC;IAC/B,0FAA0F;IAC1F,KAAK,EAAE,MAAM,GAAG,SAAS,CAAC;IAC1B,0FAA0F;IAC1F,MAAM,EAAE,eAAe,GAAG,SAAS,CAAC;IACpC,MAAM,EAAE,MAAM,CAAC;IACf,QAAQ,EAAE,OAAO,EAAE,CAAC;IACpB,eAAe,EAAE,OAAO,CAAC;CAC1B;AAED;;;;GAIG;AACH,MAAM,MAAM,eAAe,GAAG,KAAK,GAAG;IACpC,KAAK,EAAE,MAAM,CAAC;IACd,UAAU,EAAE,MAAM,CAAC;IACnB,MAAM,EAAE,eAAe,CAAC;CACzB,CAAC;AAEF,wBAAgB,iBAAiB,CAAC,KAAK,EAAE,KAAK,GAAG,KAAK,IAAI,eAAe,CAExE;AAED,MAAM,WAAW,UAAU;IACzB,SAAS,EAAE,MAAM,CAAC;IAClB,MAAM,EAAE,KAAK,EAAE,CAAC;CACjB;AAED,qBAAa,yBAA0B,SAAQ,KAAK;IAClD,YAAmB,UAAU,EAAE;QAAE,MAAM,EAAE,MAAM,CAAC;QAAC,YAAY,EAAE,SAAS,MAAM,EAAE,CAAA;KAAE,EAMjF;CACF;AAED,MAAM,WAAW,WAAW;IAC1B;;;OAGG;IACH,MAAM,IAAI,OAAO,CAAC,IAAI,CAAC,CAAC;IACxB,8DAA8D;IAC9D,KAAK,IAAI,OAAO,CAAC,UAAU,CAAC,CAAC;CAC9B;AAED,UAAU,eAAe;IACvB,MAAM,EAAE,cAAc,CAAC;IACvB,MAAM,EAAE,YAAY,CAAC;CACtB;AAED,wBAAgB,iBAAiB,CAAC,IAAI,EAAE,eAAe,GAAG,WAAW,CAUpE;AAED,wBAAgB,gBAAgB,CAAC,MAAM,EAAE,MAAM,EAAE,MAAM,EAAE,cAAc,GAAG,OAAO,CAEhF;AAgMD,UAAU,aAAa;IACrB,IAAI,EAAE,MAAM,CAAC;IACb,KAAK,EAAE,MAAM,CAAC;IACd,WAAW,EAAE,MAAM,CAAC;IACpB,UAAU,EAAE,MAAM,CAAC;IACnB,KAAK,EAAE,MAAM,CAAC;IACd,MAAM,EAAE,eAAe,CAAC;IACxB,MAAM,EAAE,MAAM,CAAC;CAChB;AAID;;;;GAIG;AACH,wBAAsB,kBAAkB,CAAC,UAAU,EAAE;IACnD,MAAM,EAAE,YAAY,CAAC;IACrB,MAAM,EAAE,cAAc,CAAC;IACvB,MAAM,EAAE,MAAM,CAAC;CAChB,GAAG,OAAO,CAAC,aAAa,CAAC,CAqDzB"}

package/dist/lib/boardSource.js

@@ -180,8 +180,10 @@ export async function fetchResolvedIssue(arguments_) {
     const { client, config, ticket } = arguments_;
     const response = await client.client.rawRequest(`query ResolveIssue($id: String!) {
       issue(id: $id) {
+        id
         title
         description
+        team { id }
         labels(first: ${ISSUE_LABEL_PAGE_SIZE}) {
           nodes { name }
         }
@@ -206,7 +208,15 @@ export async function fetchResolvedIssue(arguments_) {
     warnIfDisabledFallback(ticket, parsed, config);
     const model = parsed === undefined || parsed.model === AGENT_ANY_MODEL ? config.models.default : parsed.model;
     const runner = parsed?.runner ?? "local";
-    return { title: issue.title, description, repository, model, runner };
+    return {
+        uuid: issue.id,
+        title: issue.title,
+        description,
+        repository,
+        model,
+        runner,
+        teamId: issue.team?.id ?? "",
+    };
 }
 function parseRepository(arguments_) {
     const { description, config, repositoryRegex, ticket } = arguments_;

package/dist/lib/linearIssueStatus.d.ts

@@ -0,0 +1,17 @@
+import type { LinearClient } from "@linear/sdk";
+import type { ResolvedConfig } from "./config.ts";
+interface LinearIssueReference {
+    id: string;
+    uuid: string;
+    teamId: string;
+}
+interface LinearIssueStatusUpdater {
+    markInProgress(issue: LinearIssueReference): Promise<void>;
+    resetMissingInProgressCache(): void;
+}
+export declare function createLinearIssueStatusUpdater(arguments_: {
+    config: ResolvedConfig;
+    client: LinearClient;
+}): LinearIssueStatusUpdater;
+export {};
+//# sourceMappingURL=linearIssueStatus.d.ts.map

package/dist/lib/linearIssueStatus.d.ts.map

@@ -0,0 +1 @@
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package/dist/lib/linearIssueStatus.js

@@ -0,0 +1,41 @@
+import { log } from "./util.js";
+export function createLinearIssueStatusUpdater(arguments_) {
+    const { config, client } = arguments_;
+    const inProgressStateByTeam = new Map();
+    let teamsMissingInProgress = new Set();
+    async function getInProgressStateId(teamId) {
+        if (teamId.length === 0) {
+            return undefined;
+        }
+        const cached = inProgressStateByTeam.get(teamId);
+        if (cached !== undefined) {
+            return cached;
+        }
+        // Negative cache is reset by dispatcher each iteration so a team that's
+        // fixed in Linear during a watch session auto-recovers on the next tick.
+        if (teamsMissingInProgress.has(teamId)) {
+            return undefined;
+        }
+        const team = await client.team(teamId);
+        const states = await team.states();
+        const inProgress = states.nodes.find((state) => state.name === config.linear.statuses.inProgress);
+        if (inProgress?.id === undefined) {
+            teamsMissingInProgress.add(teamId);
+            return undefined;
+        }
+        inProgressStateByTeam.set(teamId, inProgress.id);
+        return inProgress.id;
+    }
+    async function markInProgress(issue) {
+        const stateId = await getInProgressStateId(issue.teamId);
+        if (stateId === undefined) {
+            throw new Error(`Could not find "${config.linear.statuses.inProgress}" state for ${issue.id} (team ${issue.teamId.length > 0 ? issue.teamId : "?"}). Verify the status name in linear.statuses.inProgress matches the team's workflow.`);
+        }
+        await client.updateIssue(issue.uuid, { stateId });
+        log(`Marked ${issue.id} as ${config.linear.statuses.inProgress}`);
+    }
+    function resetMissingInProgressCache() {
+        teamsMissingInProgress = new Set();
+    }
+    return { markInProgress, resetMissingInProgressCache };
+}

package/dist/lib/spriteRemoteRunnerProvider.d.ts

@@ -54,6 +54,9 @@ export interface RemoteRunnerProvider {
     runCommand(arguments_: RemoteRunArguments): Promise<string | undefined>;
     runTtyCommand(arguments_: RemoteRunArguments): Promise<void>;
     buildTtyCommand(arguments_: RemoteTtyCommandArguments): string;
+    startPortProxy(config: RemoteRunnerConfig, port: number): Promise<{
+        close(): Promise<void>;
+    }>;
     listSessions(config: RemoteRunnerConfig): Promise<string>;
     attachSession(config: RemoteRunnerConfig, target: string): Promise<void>;
     listProcesses(config: RemoteRunnerConfig): Promise<string>;

package/dist/lib/spriteRemoteRunnerProvider.d.ts.map

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package/dist/lib/spriteRemoteRunnerProvider.js

@@ -1,6 +1,12 @@
+import { connect } from "node:net";
+import { setTimeout as sleep } from "node:timers/promises";
 import { runCommandAsync } from "./commandRunner.js";
 import { shellSingleQuote } from "./shell.js";
 const LONG_RUNNING_COMMAND_OPTIONS = { stdio: "inherit", timeoutMs: 0 };
+const PROXY_CLOSE_SIGNAL = "SIGINT";
+const PROXY_READY_HOST = "127.0.0.1";
+const PROXY_READY_TIMEOUT_MS = 5000;
+const PROXY_READY_RETRY_DELAY_MS = 25;
 export const SPRITE_REMOTE_PROVIDER_DEFAULTS = {
     provider: "sprite",
     runnerName: "crew-claude-1",
@@ -155,6 +161,96 @@ async function createSpriteRunner(config) {
         timeoutMs: 0,
     });
 }
+async function startSpritePortProxy(config, port) {
+    const controller = new AbortController();
+    let closeWasRequested = false;
+    let proxyError;
+    const proxy = (async () => {
+        try {
+            await runCommandAsync("sprite", ["proxy", "-s", config.runnerName, String(port)], {
+                signal: controller.signal,
+                stdio: "inherit",
+                timeoutMs: 0,
+            });
+            if (!closeWasRequested) {
+                proxyError = new Error("Sprite proxy exited before it was closed.");
+            }
+        }
+        catch (error) {
+            if (closeWasRequested && errorHasSignal(error, PROXY_CLOSE_SIGNAL)) {
+                return;
+            }
+            proxyError = new Error(`Sprite proxy exited before it was closed: ${String(error)}`, {
+                cause: error,
+            });
+        }
+    })();
+    try {
+        await waitForSpritePortProxy({ port, proxy, proxyError: () => proxyError });
+    }
+    catch (error) {
+        closeWasRequested = true;
+        controller.abort();
+        await proxy;
+        throw error;
+    }
+    return {
+        async close() {
+            closeWasRequested = true;
+            controller.abort();
+            await proxy;
+            if (proxyError !== undefined) {
+                throw new Error(proxyError.message, { cause: proxyError });
+            }
+        },
+    };
+}
+async function waitForSpritePortProxy(arguments_) {
+    const deadline = Date.now() + PROXY_READY_TIMEOUT_MS;
+    while (Date.now() < deadline) {
+        throwIfProxyExited(arguments_.proxyError());
+        // eslint-disable-next-line no-await-in-loop -- readiness polling must observe attempts sequentially.
+        if (await canConnectToLocalPort(arguments_.port)) {
+            throwIfProxyExited(arguments_.proxyError());
+            return;
+        }
+        throwIfProxyExited(arguments_.proxyError());
+        // eslint-disable-next-line no-await-in-loop -- retry delay is bounded and stops early if the proxy exits.
+        await Promise.race([sleep(PROXY_READY_RETRY_DELAY_MS), arguments_.proxy]);
+    }
+    throwIfProxyExited(arguments_.proxyError());
+    throw new Error(`Timed out waiting for Sprite proxy on ${PROXY_READY_HOST}:${arguments_.port} to accept connections.`);
+}
+function throwIfProxyExited(error) {
+    if (error !== undefined) {
+        throw new Error(error.message, { cause: error });
+    }
+}
+async function canConnectToLocalPort(port) {
+    return await new Promise((resolve) => {
+        const socket = connect({ host: PROXY_READY_HOST, port });
+        socket.once("connect", () => {
+            socket.destroy();
+            resolve(true);
+        });
+        socket.once("error", () => {
+            socket.destroy();
+            resolve(false);
+        });
+    });
+}
+function errorHasSignal(error, signal) {
+    if (typeof error !== "object" || error === null) {
+        return false;
+    }
+    if ("signal" in error && error.signal === signal) {
+        return true;
+    }
+    if (error instanceof Error && error.cause !== undefined) {
+        return errorHasSignal(error.cause, signal);
+    }
+    return false;
+}
 export const spriteRemoteRunnerProvider = {
     name: "sprite",
     async runnerExists(config) {
@@ -174,6 +270,9 @@ export const spriteRemoteRunnerProvider = {
         });
     },
     buildTtyCommand: buildSpriteTtyCommand,
+    async startPortProxy(config, port) {
+        return await startSpritePortProxy(config, port);
+    },
     async listSessions(config) {
         const output = await runCommandAsync("sprite", ["sessions", "list", "-s", config.runnerName], {
             trim: false,

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clipboard-health/groundcrew",
-  "version": "1.10.1",
+  "version": "1.11.0",
   "description": "Linear-driven orchestrator that launches AI coding agents in git worktrees, with workspace lifecycle, remote runners, and usage tracking.",
   "keywords": [
     "agent",
@@ -84,7 +84,7 @@
     "husky": "9.1.7",
     "jscpd": "4.0.9",
     "knip": "6.9.0",
-    "lint-staged": "16.4.0",
+    "lint-staged": "17.0.4",
     "markdownlint-cli2": "0.22.1",
     "nx": "22.7.1",
     "oxfmt": "0.47.0",