auspex: IT Admin User Guide for Rippling (macOS)

Last updated: August 20, 2026

This guide is for IT administrators deploying the Span agent (auspex) to macOS devices via Rippling.

What This Package Does

auspex captures AI coding activity (prompts, file edits, tool use) from supported IDEs (Cursor, Claude Code, Codex, and more) and sends telemetry to Span's analytics backend. This data appears in your Span dashboard under AI Effectiveness.

The macOS installer is a single universal .pkg. When it installs elevated (as Rippling does), it places the binary at /usr/local/bin/auspex, drops a root-owned managed configuration at /Library/Application Support/auspex/ (the managed.yaml marker = managed mode), and converges automatically (postinstall runs auspex install --system, wires machine-wide hooks, provisions each engineer's identity, and starts the per-user agent at login).

No separate "install hooks" step is needed — the package converges itself. Your job is to (a) pre-authorize file access so users are never prompted, and (b) deliver each device's identity (token + work email) before the package installs.

Prerequisites

  • A Span account with access to integration settings.
  • A Rippling account with Device Management, and target macOS devices (macOS 13+, supervised) enrolled and grouped.
  • Each engineer's work email in Rippling (used to identify the individual on their device).
  • The macOS package: https://auspex.span.app/releases/v0.1.0/darwin/auspex_0.1.0_darwin_universal.pkg.

Deployment order (important)

  1. Custom Profile (file access + background items) — first.
  2. The package (Software) with the identity pre-install script attached — so identity lands immediately before the package converges.

Step 1: Enable the Integration and Get Your Token (one-time)

This step is the same regardless of your MDM.

Head to the AI tool settings dashboard (https://span.app/_/settings/integrations) and under IDE & CLI AI Tool Integrations, enable the tools your engineers use:

Tool What's captured
Claude Code OTEL metrics + hooks
Cursor Hooks
Codex CLI OTEL metrics + hooks
Copilot CLI Hooks
VSCode chat Hooks

If a tool has no dashboard toggle, enable Claude Code or Codex CLI to generate the (org-wide) token.

Step 2: Deploy the File-Access + Background-Items Profile (before the package)

auspex reads the edited file from the git working tree the moment an AI edit fires. For users with repos under a TCC-protected folder (Documents, Desktop, Downloads), that would prompt:

"auspex" would like to access files in your Documents folder.

Deploy the combined profile before the package so no one is prompted. It grants Full Disk Access (PPPC), pre-approves auspex's background items, and silences the background-activity notification.

  1. In Rippling: Devices → Custom Profiles → Add Custom Profile (upload a .mobileconfig).
  2. Upload auspex-background-items.mobileconfig.
  3. Assign to the same devices/group that will receive the package.

The profile ships with Span's Developer ID team (KNH44SBYN4) and binary path pre-filled. Confirm against a deployed Mac if needed: codesign -dr - /usr/local/bin/auspex.

Requires a supervised device from a trusted MDM (macOS 13+).

Step 3: Deploy the Package with an Identity Pre-Install Script

Deliver the identity file from a pre-install script attached to the package, so it lands before the package converges. The script runs as root and injects the assigned employee's work email via a Rippling attribute variable.

#!/bin/bash
set -euo pipefail

# REQUIRED: paste your org token from Step 1
TOKEN="<YOUR_TOKEN>"
# Replace with Rippling's variable for the assigned employee's work email
# (confirm the exact token in the Rippling script editor); resolves per-device.
EMAIL="__RIPPLING_WORK_EMAIL_VARIABLE__"

if [ -z "$EMAIL" ] || [[ "$EMAIL" != *"@"* ]]; then
  echo "ERROR: could not resolve work email." >&2
  exit 1
fi

DIR="/Library/Application Support/auspex"
mkdir -p "$DIR"
printf '{\n  "token": "%s",\n  "work_email": "%s"\n}\n' "$TOKEN" "$EMAIL" > "$DIR/identity.json"
chown root:wheel "$DIR/identity.json"
chmod 644 "$DIR/identity.json"
echo "Success: identity.json written for $EMAIL"

To deploy:

  1. In Rippling: Devices → Software → Upload Software.
  2. Set Operating System to macOS, and provide the .pkg (upload it, or point at the package URL above).
  3. Attach the script above as the Pre-install script. This guarantees identity.json exists before the package converges.
  4. Submit, then assign to your target devices/group (the same as Step 2).

On install, the package converges the device to managed mode and starts the daemon.

Step 4: Smoke Test (before fleet rollout)

Assign Steps 2–3 to 1–2 pilot devices first. Confirm the pre-install script and the package both report success in Rippling, then on-device:

pkgutil --pkg-info app.span.auspex
auspex status        # stderr: install mode: managed
auspex auth show     # work email + MASKED token

Then confirm System Settings → Privacy & Security → Full Disk Access shows auspex enabled and "managed by your organization," and that the pilot user's traces appear in the dashboard after using a coding tool.

Optional: Replace legacy Span coding-hooks in the same rollout

If you're migrating from the older coding-hooks agent, you can retire it on each device as part of this rollout. This step is optional and best-effort: it removes coding-hooks only after auspex is confirmed installed, and only if the coding-hooks uninstaller is present — so it's safe to assign fleet-wide, including to devices that never had coding-hooks (there it simply no-ops).

Why bundle it: until coding-hooks is removed, a device running both agents will capture and send each event twice (duplicate traces). Gating removal on a confirmed auspex install lets you cut over cleanly, one device at a time, with no window where neither agent is running.

In Rippling: attach this as the software item's Post-install script (Step 3), or add it as a separate Custom Script. Either way the self-gate keeps it safe — as a standalone script it simply no-ops until auspex is confirmed, then removes coding-hooks.

#!/bin/bash
# OPTIONAL post-install: retire legacy Span coding-hooks AFTER a confirmed auspex install.
# Safe anywhere — no-ops unless auspex is fully installed, and only removes coding-hooks
# if its uninstaller is present. Never fails the calling MDM step (always exits 0).
set -uo pipefail

CH_UNINSTALL="/Library/Application Support/app.span.coding-hooks/uninstall.sh"

# Gate 1 — auspex package receipt present (install confirmed by macOS).
if ! /usr/sbin/pkgutil --pkg-info app.span.auspex >/dev/null 2>&1; then
  echo "auspex receipt not found — install not confirmed; leaving coding-hooks in place."
  exit 0
fi

# Gate 2 — auspex binary AND managed marker both in place.
if [ ! -x "/usr/local/bin/auspex" ] || [ ! -f "/Library/Application Support/auspex/managed.yaml" ]; then
  echo "auspex not fully in place (binary or managed marker missing) — leaving coding-hooks in place."
  exit 0
fi

# auspex confirmed — best-effort remove coding-hooks, only if its uninstaller exists.
if [ -f "$CH_UNINSTALL" ]; then
  echo "auspex confirmed — removing legacy coding-hooks…"
  bash "$CH_UNINSTALL" || echo "coding-hooks uninstall returned non-zero (best-effort) — continuing."
  echo "Done: coding-hooks removal attempted."
else
  echo "No coding-hooks uninstaller found — nothing to remove."
fi
exit 0

Notes:

  • The script exits 0 on every path, so a coding-hooks removal failure never fails the MDM step or disturbs auspex.
  • It removes coding-hooks only when both auspex gates pass and the uninstaller exists at /Library/Application Support/app.span.coding-hooks/uninstall.sh. On any other device it reports what it skipped and exits cleanly.
  • User-defined hooks in Cursor and Claude Code are preserved by the coding-hooks uninstaller.

Troubleshooting

Symptom Remediation
Config holds a placeholder token Re-run Step 3; confirm the real token replaced <YOUR_TOKEN>
Missing / wrong work email Confirm the Rippling work-email variable resolves for the assigned employee
Package never installs Confirm the device is enrolled and has checked in; check the software item's assignment
Managed, but capture unauthenticated Package converged before identity existed — confirm auspex auth show, then re-run sudo auspex install --system
User prompted for Documents access Step 2 profile wasn't in place first — deploy it, then sudo tccutil reset SystemPolicyAllFiles
No data in dashboard Check identity, have the user run a coding tool, confirm the feature is enabled for your org

Upgrading

Upload the new package version to the existing Software item (re-attaching the pre-install script). Assigned devices reinstall on next check-in; managed.yaml and edited policy are preserved.

Uninstalling

auspex ships two removers, one per tier. auspex uninstall removes a user-tier (self-installed) agent — its per-user service, binary, and hooks. auspex hooks uninstall --system un-wires the managed (machine-wide) capture hooks. Neither removes the machine-wide binary, launchd units, or root-owned managed config the package placed — a macOS .pkg has no built-in uninstaller and there is no auspex uninstall --system. So a clean managed removal runs both commands, then removes those machine-wide artifacts, then removes the MDM-delivered profiles.

Step 1 — Uninstall auspex

Run it elevated on the device, or deliver it through Rippling (as a Custom Script). It un-wires the hooks first (while the binary still exists), then removes the daemon units, the managed config, the binary, and the package receipt:

#!/bin/bash
set -uo pipefail
BIN="/usr/local/bin/auspex"   # full path: root/MDM shells often omit /usr/local/bin from PATH

# 1a. Un-wire the MANAGED (machine-wide) capture hooks — the tier the MDM package wired.
"$BIN" hooks uninstall --system || true
# 1b. Clean up any lingering USER-tier install (e.g. a self-install from before the device
#     was enrolled). `auspex uninstall` ONLY touches the per-user tier — it does not remove
#     the managed tier, which is why 1a and the machine-wide removals below are still needed.
"$BIN" uninstall || true

# 2. Stop and remove the launchd units. Boot out the converge LaunchDaemon (system domain) AND
#    the per-user daemon LaunchAgent for every logged-in user (gui/<uid>), then remove the plists.
launchctl bootout system "/Library/LaunchDaemons/app.span.auspex.converge.plist" 2>/dev/null || true
for u in /Users/*; do uid=$(id -u "$(basename "$u")" 2>/dev/null) || continue
  launchctl bootout "gui/$uid" "/Library/LaunchAgents/app.span.auspex.plist" 2>/dev/null || true
done
rm -f "/Library/LaunchDaemons/app.span.auspex.converge.plist" "/Library/LaunchAgents/app.span.auspex.plist"

# 3. Remove the root-owned managed config tree (clear its tamper-proof ACL first).
chmod -N "/Library/Application Support/auspex" 2>/dev/null || true
rm -rf "/Library/Application Support/auspex"

# 4. Remove the binary and forget the package receipt.
rm -f "$BIN"
pkgutil --forget app.span.auspex 2>/dev/null || true

echo "auspex uninstalled"

On a self-installed (non-managed) Mac, auspex uninstall on its own is the complete uninstaller — see the self-install guide. On a managed device it only clears a user-tier remnant, so the managed steps above are still required.

Step 2 — Remove the MDM-delivered profiles and assignment

In Rippling, remove the Software item from the target group (Rippling uninstalls on next check-in) and unassign the Step 2 profile, and remove any tamper/removal lock first. Do this so the MDM does not re-deliver auspex on the next check-in.

Verify the removal is complete

Run on the device — every line should print ok: (no receipt, binary, config, or daemon left):

pkgutil --pkg-info app.span.auspex >/dev/null 2>&1 && echo "STILL PRESENT: package receipt" || echo "ok: no package receipt"
command -v auspex >/dev/null 2>&1 && echo "STILL PRESENT: auspex on PATH ($(command -v auspex))" || echo "ok: auspex not on PATH"
[ -e /usr/local/bin/auspex ] && echo "STILL PRESENT: /usr/local/bin/auspex" || echo "ok: binary gone"
[ -e "/Library/Application Support/auspex" ] && echo "STILL PRESENT: managed config tree" || echo "ok: managed config gone"
launchctl print system/app.span.auspex.converge >/dev/null 2>&1 && echo "STILL LOADED: converge daemon" || echo "ok: converge daemon not loaded"
CU=$(stat -f%u /dev/console 2>/dev/null || echo 0); launchctl print "gui/$CU/app.span.auspex" >/dev/null 2>&1 && echo "STILL LOADED: per-user daemon (gui/$CU)" || echo "ok: per-user daemon not loaded"
ls /Library/LaunchDaemons/app.span.auspex.converge.plist /Library/LaunchAgents/app.span.auspex.plist >/dev/null 2>&1 && echo "STILL PRESENT: launchd units" || echo "ok: launchd units gone"

Fallback — only if the checks above still show remnants

A leftover usually means the tamper-proof ACL blocked removal, a launchd unit was still loaded, or an MDM profile re-pushed the managed config before Step 2 completed. First confirm Step 2 removed the MDM assignment (so nothing re-delivers), then force the removal:

#!/bin/bash
launchctl bootout system "/Library/LaunchDaemons/app.span.auspex.converge.plist" 2>/dev/null || true
# Boot out the per-user daemon agent for every user, best-effort.
for u in /Users/*; do uid=$(id -u "$(basename "$u")" 2>/dev/null) || continue
  launchctl bootout "gui/$uid" "/Library/LaunchAgents/app.span.auspex.plist" 2>/dev/null || true
done
rm -f "/Library/LaunchDaemons/app.span.auspex.converge.plist" "/Library/LaunchAgents/app.span.auspex.plist"
chmod -R -N "/Library/Application Support/auspex" 2>/dev/null || true
rm -rf "/Library/Application Support/auspex"
rm -f /usr/local/bin/auspex
pkgutil --forget app.span.auspex 2>/dev/null || true
echo "auspex force-removed — re-run the verify checks above"

User-defined hooks in Cursor and Claude Code are preserved throughout.

Support

For issues not covered here, contact the Span team with:

auspex status
auspex support        # redacted support bundle