prepare-to-send

Prepare to Send

The last gate before a PDF goes out. This skill drives the checklist section-by-section, delegates metadata scrubbing to scrub-pdf-metadata, collects results, and refuses to declare "ready" unless every gate passes.

When to use

• Before attaching a CV PDF to an application form or email
• After export-pdf and before the user hits "send"
• On demand when the user wants reassurance the file is clean

Inputs

• PDF file (optional argument $1): the PDF to audit. Resolution order:
  1. If $1 is passed → use it directly.
  2. Else if CWD contains a sibling company.md (i.e. CWD is a per-company folder) → pick the *_CV.pdf in CWD; if multiple, take the one with the most recent mtime.
  3. Else → hard error: "No PDF specified and CWD is not a per-company folder. Pass a path or cd into a company folder."
• HTML counterpart: inferred by swapping .pdf → .html on the same stem in the same directory.

Workspace root

Derive the workspace root from the environment:

workspace="${JOB_HUNT_WORKSPACE:-$HOME/Documents/job_seeking}"

Use ls -1 "$workspace" to enumerate company folders when needed (e.g. cross-company leak checks).

Preconditions

Hard-require exiftool up front. Do NOT degrade; a partial audit is worse than no audit because it creates false confidence.

command -v exiftool >/dev/null 2>&1 || { echo "ERROR: exiftool not installed (brew install exiftool)"; exit 1; }

If missing, stop immediately. Do not run any section.

Workflow

Run each section top to bottom and record PASS/FAIL. ANY fail = stop, report the failing section, do not proceed to the next. Do not issue warnings — everything is either pass or fail.

---

Section 1 — Filename sanity

Validate the PDF filename against ${PLUGIN_ROOT}/references/naming-rules.md.

Checklist:

• Matches <First>_<Last>_<Role>_<DocType>.pdf
• No spaces, pipes |, commas, slashes, emojis, or non-ASCII characters in the filename (hyphens are allowed)
• No company name anywhere in the filename
• Length ≤ 70 chars
• Extension is .pdf exactly

---

Section 2 — HTML + PDF parity

Checklist:

• HTML file with same stem exists in the same directory
• HTML mtime ≤ PDF mtime (PDF not stale)

if [[ "$(stat -f%m "$html")" -gt "$(stat -f%m "$pdf")" ]]; then
  echo 'FAIL: HTML edited after PDF exported. Re-run $job-hunt-toolkit:export-pdf.'
  exit 1
fi

---

Section 3 — PDF metadata scrub

Invoke the scrub-pdf-metadata skill on the PDF; do not inline exiftool commands here.

If the skill cannot be invoked as a skill, fall back to the exact commands from ${PLUGIN_ROOT}/skills/scrub-pdf-metadata/references/exiftool-commands.md under "One-liner: scrub + set + verify" — never improvise.

After scrub, verify with:

exiftool -Title -Author -Producer -Creator -CreatorTool -CreateDate -Keywords -Subject "$pdf"

Checklist:

• Title = "CV" (generic)
• Author = clean legal name
• Producer / Creator empty or "exiftool" only
• Keywords empty
• Subject empty
• No XMP custom fields mentioning paths, companies, or other identifying strings
• No embedded file path strings

Fail if Title ≠ "CV", if Keywords or Subject are non-empty, or if any field contains a path or another company name.

---

Section 4 — Visible content scan

4a. PDF text

Use the Read tool on the PDF to extract its text. Scan the extracted content for:

• TODO, FIXME, XXX, [placeholder], {{, <role>
• draft, v1, v2, v3, final as standalone markers
• Absolute path fragments: /Users/, /home/, C:\, file://
• ANY company name other than the one being applied to — cross-reference the workspace's per-company folder names

Cross-company leak check:

current_company="$(basename "$(dirname "$pdf")")"
other_companies="$(ls -1 "$workspace" 2>/dev/null | grep -v "^${current_company}$" | grep -v '^\.' || true)"

Fail on ANY hit for another company name in the PDF text.

@page CSS path leak: Some HTML templates embed source paths in headers/footers via @page CSS. When scanning PDF text, also look for file:, /Users/, /home/, or the workspace basename from $(basename "${JOB_HUNT_WORKSPACE:-$HOME/Documents/job_seeking}"). Any match means the @page rule leaked the build path into the rendered output.

Rasterized PDF check: After reading the PDF, verify extracted text is at least 200 characters long (configurable via JOB_HUNT_MIN_PDF_TEXT_CHARS). If it fails, report: "FAIL: PDF text extraction yielded fewer than $min_chars chars. Likely rasterized. Re-export."

Checklist:

• No template markers (TODO, FIXME, XXX, [placeholder], {{)
• No standalone draft/version markers
• No other-company names
• No absolute path fragments
• No email addresses or phone numbers that are not the user's
• Contact info present and correct (email, LinkedIn URL, phone if included)
• PDF text length ≥ 200 chars (not rasterized)

4b. HTML comments

grep -oE '<!--[^>]*-->' "$html" || true

Block HTML comments that reference another company; commented-out prior-application bullets are high-risk because some PDF indexers parse comments.

Checklist:

• No <!-- ... --> comments referencing other companies
• No commented-out bullets from prior tailoring sessions
• No TODO comments to self

---

Section 5 — Sensitive file presence

Check for sensitive files in the workspace that should not travel with the application.

Checklist:

• No .env, *.key, id_rsa, *.local.md, secrets.*, or salary_notes.md in the application folder (unless user has explicitly confirmed their presence is intentional)

find "$(dirname "$pdf")" -maxdepth 2 \( \
  -name '.env' -o -name '*.key' -o -name 'id_rsa' \
  -o -name '*.local.md' -o -name 'secrets.*' -o -name 'salary_notes.md' \
\) 2>/dev/null

If any are found, stop and report them. Do not proceed.

---

Section 6 — PDF rendering sanity

Use the Read tool on the PDF and verify:

• PDF opens without error
• Text is selectable (not rasterized) — required for ATS
• Page count matches expectation (usually 1–2 pages for a CV)
• Links (LinkedIn, portfolio, email) are present

Reuse Section 4a's JOB_HUNT_MIN_PDF_TEXT_CHARS threshold; if it passed there, record PASS here.

---

Section 7 — Content correctness

The assistant must read both the PDF text and accompanying company.md / job_description.*, then verify:

• Name spelling correct
• Dates consistent (no contradictions between roles)
• Company names in work history spelled correctly
• No fabricated experience or inflated seniority beyond defensible (cross-check against master CV)
• Role title on the CV sensibly matches / reframes the target JD's role
• Key must-have JD requirements are visibly addressed in the CV text

Also read the master HTML. Any discrepancy = fail with a specific line-level finding.

---

Section 8 — company.md present and current

Verify the per-company file exists and has been updated beyond template defaults.

company_md="$(dirname "$pdf")/company.md"
[[ -f "$company_md" ]] || { echo "FAIL: company.md missing in application folder."; exit 1; }

Checklist:

• company.md exists in the application folder
• status field reflects current reality (valid values: drafting | applied | screening | interview | offer | signed | rejected | withdrew)

If status is still drafting, surface it as informational so the user can update it after sending; do not fail.

---

Section 9 — Final sanity

Ask the user to confirm these judgment calls via AskUserQuestion; they are not automated gates.

• Open PDF in a different renderer than the one that made it (Preview if exported via Chrome; vice-versa) to catch tool-specific bugs
• Re-read the first sentence of the first bullet — does it instantly signal fit for THIS role?
• Imagine the recruiter's 6-second scan — is the best thing about the candidate for this role visible first?

---

Report

Only print the full summary if all automated sections pass:

Pre-send audit: <pdf-filename>

[PASS] Filename sanity
[PASS] HTML/PDF pair in sync
[PASS] Metadata scrubbed (Title=CV, Author=<clean name>)
[PASS] Visible content — 0 leaks
[PASS] Sensitive file presence
[PASS] PDF rendering (<chars> text chars)
[PASS] Content correctness (name / dates / companies / no hallucinations)
[PASS] company.md present

Judgment-call gates (confirm with user):
  - Alternate renderer preview OK?
  - First-bullet fit signal strong?
  - 6-second scan surfaces best angle?

Ready to send.

Attach: <absolute-path-to-pdf>

If any automated section fails, print ONLY the failing section's diagnostic and stop. Do not continue.

---

Hard rules

• Every automated gate must pass — no warnings, no partial pass. Partial pass = fail.
• Require exiftool up front. No silent degradation. Missing tool = abort.
• Always run scrub-pdf-metadata in Section 3. Never skip even if the user says they "just scrubbed" — HTML edits invalidate prior scrubs.
• Cross-company leak = catastrophic. Any other company name in the PDF text or HTML comments is game-over; block.
• Defer metadata specifics to scrub-pdf-metadata and its references. If you need to fall back, use EXACT commands from exiftool-commands.md — never improvise.