Gmail Access

Gmail Access

Read and search Gmail programmatically via Claude Code.

Self-Evolving Skill: This skill improves through use. If instructions are wrong, parameters drifted, or a workaround was needed — fix this file immediately, don't defer. Only update for real, reproducible issues.

MANDATORY PREFLIGHT (Execute Before Any Gmail Operation)

CRITICAL: You MUST complete this preflight checklist before running any Gmail commands. Do NOT skip steps.

Step 1: Check CLI Binary Exists

ls -la "$HOME/.claude/plugins/marketplaces/cc-skills/plugins/gmail-commander/scripts/gmail-cli/gmail" 2>/dev/null || echo "BINARY_NOT_FOUND"

If BINARY_NOT_FOUND: Build it first:

cd ~/.claude/plugins/marketplaces/cc-skills/plugins/gmail-commander/scripts/gmail-cli && bun install && bun run build

Step 2: Check GMAIL_OP_UUID Environment Variable

echo "GMAIL_OP_UUID: ${GMAIL_OP_UUID:-NOT_SET}"

If NOT_SET: You MUST run the Setup Flow below. Do NOT proceed to Gmail commands.

Step 2.5: Verify Account Context (CRITICAL)

ALWAYS verify you're accessing the correct email account for the current project.

# Show current project context
echo "=== Gmail Account Context ==="
echo "Working directory: $(pwd)"
echo "GMAIL_OP_UUID: ${GMAIL_OP_UUID}"

# Check where GMAIL_OP_UUID is defined (mise hierarchy)
echo ""
echo "=== mise Config Source ==="
grep -l "GMAIL_OP_UUID" .mise.local.toml .mise.toml ~/.config/mise/config.toml 2>/dev/null || echo "Not found in standard locations"

# Quick connectivity test — shows the account email from a real email
echo ""
echo "=== Account Verification ==="
$GMAIL_CLI list -n 1 2>&1 | head -5

STOP and confirm with user before proceeding:

• The list -n 1 output shows the account's inbox — verify this matches the project's intended email
• If the wrong account is shown, check which .mise.local.toml sets GMAIL_OP_UUID in the mise hierarchy
• If mismatch, inform user and do NOT proceed

Multi-account disambiguation (when GMAIL_OP_UUID is NOT_SET but tokens exist). There is no whoami subcommand; map each cached token UUID to its mailbox by probing, then pick the one that fits the project:

🔴 Do NOT identify a mailbox from list -n 1 --json | jq '.[0].to'. That reads the recipient of the newest message, not the mailbox owner. When the newest item is an outgoing draft or a sent message, it reports the person you wrote TO. Measured 2026-08-18: the wc6vl… token probed as an external correspondent's address while the mailbox is in fact amonic@gmail.com — a confident wrong answer in the one step whose entire job is to stop you acting on the wrong account.

Ask Gmail who it is instead. users/me/profile is authoritative:

# Which accounts are cached, and which mailbox does each ACTUALLY own?
for f in ~/.claude/tools/gmail-tokens/*.json; do
  case "$(basename "$f")" in *.app-credentials.json|*.bak|*.expired-*|*.dead-*|'*.json') continue ;; esac
  uuid=$(basename "$f" .json)
  # Project-local helper that mints an access token from a cached refresh token.
  tok=$(bash "${GMAIL_TOKEN_SCRIPT:?set to your project's gmail-access-token.sh}" "$uuid" 2>/dev/null | tail -1)
  if [ -z "$tok" ]; then echo "$uuid → token mint failed"; continue; fi
  who=$(curl -s --noproxy '*' -H "Authorization: Bearer $tok" \
          https://gmail.googleapis.com/gmail/v1/users/me/profile | jq -r .emailAddress)
  echo "$uuid → $who"
done

The same endpoint answers "which aliases may I send as", which you need before any --from. verificationStatus must be accepted, and note which alias is isDefault — if the default is not the one you want, --from is mandatory, not optional:

curl -s --noproxy '*' -H "Authorization: Bearer $tok" \
  https://gmail.googleapis.com/gmail/v1/users/me/settings/sendAs \
  | jq -r '.sendAs[] | "\(.sendAsEmail)\t\(.verificationStatus)\t\(if .isDefault then "DEFAULT" else "" end)"'

A probe that returns invalid_grant means that account's refresh token is dead (see "Diagnosing invalid_grant"). Pick the working UUID whose mailbox matches the project, pin it in .mise.local.toml, and confirm it's gitignored. A child project often needs a DIFFERENT account than its parent — verify, never assume the parent's UUID.

Step 3: Verify Token Health

# Check cached token exists and is not expired
TOKEN_FILE="$HOME/.claude/tools/gmail-tokens/${GMAIL_OP_UUID}.json"
APP_CREDS="$HOME/.claude/tools/gmail-tokens/${GMAIL_OP_UUID}.app-credentials.json"
echo "Token file: $([ -f "$TOKEN_FILE" ] && echo "EXISTS" || echo "MISSING")"
echo "App credentials: $([ -f "$APP_CREDS" ] && echo "CACHED" || echo "MISSING — will need 1Password on first run")"

If token file is MISSING: First run will open a browser for OAuth consent. This is expected. If app credentials are MISSING: 1Password will be called once to cache client_id/client_secret, then never again.

Setup Flow (When GMAIL_OP_UUID is NOT_SET)

Follow these steps IN ORDER. Use AskUserQuestion at decision points.

Setup Step 1: Check 1Password CLI

command -v op && echo "OP_CLI_INSTALLED" || echo "OP_CLI_MISSING"

If OP_CLI_MISSING: Stop and inform user:

1Password CLI is required. Install with: brew install 1password-cli

Setup Step 2: Discover Gmail OAuth Items in 1Password

# Try common vaults — "Claude Automation" for service accounts, "Employee" for interactive
for VAULT in "Claude Automation" "Employee" "Personal"; do
  ITEMS=$(op item list --vault "$VAULT" --format json 2>/dev/null | jq -r '.[] | select(.title | test("gmail|oauth|google"; "i")) | "\(.id)\t\(.title)"')
  [ -n "$ITEMS" ] && echo "=== Vault: $VAULT ===" && echo "$ITEMS"
done

Parse the output and proceed based on results:

Setup Step 3: User Selects OAuth Credentials

If items found, use AskUserQuestion with discovered items:

AskUserQuestion({
  questions: [{
    question: "Which 1Password item contains your Gmail OAuth credentials?",
    header: "Gmail OAuth",
    options: [
      // POPULATE FROM op item list RESULTS - example:
      { label: "Gmail API - dental-quizzes (56peh...)", description: "OAuth client in Employee vault" },
      { label: "Gmail API - personal (abc12...)", description: "Personal OAuth client" },
    ],
    multiSelect: false
  }]
})

If NO items found, use AskUserQuestion to guide setup:

AskUserQuestion({
  questions: [{
    question: "No Gmail OAuth credentials found in 1Password. How would you like to proceed?",
    header: "Setup",
    options: [
      { label: "Create new OAuth credentials (Recommended)", description: "I'll guide you through Google Cloud Console setup" },
      { label: "I have credentials elsewhere", description: "Help me add them to 1Password" },
      { label: "Skip for now", description: "I'll set this up later" }
    ],
    multiSelect: false
  }]
})

• If "Create new OAuth credentials": Read and present references/gmail-api-setup.md
• If "I have credentials elsewhere": Guide user to add to 1Password with required fields
• If "Skip for now": Inform user the skill won't work until configured

Setup Step 4: Confirm mise Configuration

After user selects an item (with UUID), use AskUserQuestion:

AskUserQuestion({
  questions: [{
    question: "Add GMAIL_OP_UUID to .mise.local.toml in current project?",
    header: "Configure",
    options: [
      { label: "Yes, add to .mise.local.toml (Recommended)", description: "Creates/updates gitignored config file" },
      { label: "Show me the config only", description: "I'll add it manually" }
    ],
    multiSelect: false
  }]
})

If "Yes, add to .mise.local.toml":

1. Check if .mise.local.toml exists
2. If exists, append GMAIL_OP_UUID to [env] section
3. If not exists, create with:

[env]
GMAIL_OP_UUID = "<selected-uuid>"

1. Verify .mise.local.toml is in .gitignore

If "Show me the config only": Output the TOML for user to add manually.

Setup Step 5: Reload and Verify

mise trust 2>/dev/null || true
cd . && echo "GMAIL_OP_UUID after reload: ${GMAIL_OP_UUID:-NOT_SET}"

If still NOT_SET: Inform user to restart their shell or run source ~/.zshrc.

Setup Step 6: Test Connection

GMAIL_OP_UUID="${GMAIL_OP_UUID}" $HOME/.claude/plugins/marketplaces/cc-skills/plugins/gmail-commander/scripts/gmail-cli/gmail list -n 1

If OAuth prompt appears: This is expected on first run. Browser will open for Google consent.

Gmail Commands (Only After Preflight Passes)

GMAIL_CLI="$HOME/.claude/plugins/marketplaces/cc-skills/plugins/gmail-commander/scripts/gmail-cli/gmail"

# List recent emails
$GMAIL_CLI list -n 10

# Search emails
$GMAIL_CLI search "from:someone@example.com" -n 20

# Search with date range
$GMAIL_CLI search "from:alice after:2026/01/27" -n 10

# Read specific email with full body
$GMAIL_CLI read <message_id>

# Read and download inline images (copy-pasted screenshots in compose)
$GMAIL_CLI read <message_id> --save-images

# Download inline images to a specific directory
$GMAIL_CLI read <message_id> --save-images --image-dir ./attachments/my-folder/

# Shorthand: --image-dir implies --save-images
$GMAIL_CLI read <message_id> --image-dir ./attachments/my-folder/

# JSON output with image metadata and saved paths
$GMAIL_CLI read <message_id> --save-images --json

# Download REAL file attachments (PDF, docx, csv, …) — distinct from inline images
$GMAIL_CLI read <message_id> --save-attachments

# Download attachments to a specific directory (implies --save-attachments)
$GMAIL_CLI read <message_id> --attachment-dir ./files/case-17402939/

# Export search results to JSON (full body + inlineImages + attachments metadata per message)
$GMAIL_CLI export -q "label:inbox" -o emails.json -n 100

# JSON output (for parsing)
$GMAIL_CLI list -n 10 --json

# Create a draft email
$GMAIL_CLI draft --to "user@example.com" --subject "Hello" --body "Message body"

# Create a draft reply (threads into existing conversation)
$GMAIL_CLI draft --to "user@example.com" --subject "Re: Hello" --body "Reply text" --reply-to <message_id>

# Draft with body loaded from a file (multi-paragraph bodies are awkward via --body)
$GMAIL_CLI draft --to "user@example.com" --subject "Report" --body-file ./email-body.txt

# Draft with file attachments (--attach is repeatable; MIME type guessed from extension)
$GMAIL_CLI draft --to "user@example.com" --subject "Q1 Report" \
  --body-file ./email-body.txt \
  --attach ./report.pdf \
  --attach ./screenshot.png

# Draft reply with both body-file and multiple attachments
$GMAIL_CLI draft --to "user@example.com" --subject "Re: Project" \
  --reply-to <message_id> \
  --body-file ./reply.txt \
  --attach ./diagram.pdf

# List drafts with their draft IDs
$GMAIL_CLI drafts -n 10

# Replace a draft in place (delete + recreate — the draft ID CHANGES)
$GMAIL_CLI draft-update <draft_id> --to "user@example.com" --from "me@example.com" \
  --subject "Same subject" --body-file ./revised-body.txt

drafts --json field names

The identifier field is draftId, not id. A .id selector silently yields null for every row rather than erroring, so a jq pipeline built on it looks like it worked and hands you nothing:

# WRONG — .id does not exist; prints "null" per draft and fails silently
$GMAIL_CLI drafts -n 10 --json | jq -r '.[] | "\(.id)\t\(.subject)"'

# RIGHT
$GMAIL_CLI drafts -n 10 --json | jq -r '.[] | "\(.draftId)\t\(.subject)"'

Full row shape: date, draftId, from, messageId, snippet, subject, threadId, to. Note the two distinct identifiers — draftId is what draft-update and draft-delete take; messageId is what read takes. Passing one where the other belongs fails or returns the wrong record.

draft-update returns a NEW draftId (it deletes and recreates). Any ID you noted earlier is dead the moment you update — re-list before a second update, and never cache a draft ID across edits.

🔴 ATTRIBUTION DOCTRINE — run this before you ever write "they said X"

Reading an email and knowing who wrote which line are two different problems. The second one is harder, its answer is not in the text you get back by default, and when it goes wrong it does not throw — it produces a fluent, confident summary in which your own sentences are attributed to your correspondent, or half of what they wrote is silently missing. Every failure recorded in this section was of that shape: a wrong query returning an empty result, read as an empty world.

This applies by default. If a message is a reply — it has quoted history — and you intend to quote, summarise, attribute, decide, or act on what the sender said, you run the protocol below. It does not apply to listing, searching, triage, or counting.

The model: authorship ⊃ colour ⊃ marker

Three signals, nested, in descending order of trust. Using the wrong one as your primary is how both halves of the 2026-08-25 incident happened.

The protocol

bun scripts/attribution-parse.ts --id <messageId> --token-cmd '<cmd printing an access token>'

It prints which signals are actually present, what it attributes to the sender and why, and — the important part — what it cannot attribute. It reports CONFLICT when signals disagree and UNKNOWN when a line at quoted depth carries neither colour nor marker, because in that case the line genuinely could belong to either party. UNKNOWN is a correct answer. A tool that always decides is a tool that is sometimes confidently wrong.

Four rules that outlive any particular client

1. Verify the convention per message. Never infer it from another message. The same correspondent used three different conventions in six days: css-coloured on 20 Aug, >>>PT markers with no colour at all on 21 Aug, legacy <font color> on 25 Aug. A message that says "see my comments in blue" may contain no colour whatsoever — measured, twice.
2. An empty result from a detector means your detector might be wrong. This is the single most expensive habit in this file. Zero colour spans, zero markers, zero matching rows — before concluding the sender did not do the thing, prove your query can find the thing when it is there. Same shape as the .[0].to mailbox probe and the .id draft field elsewhere in this skill.
3. Read to the end of the paragraph. An audit of 22 authored segments found the residual misses were not caused by parsing at all — every one sat inside a segment already extracted, and was lost to first-sentence reading. Her structure is consistent and it is the opposite of a summary: the decision is in sentence one, the condition is in sentence two, and the condition is the part that binds you. "Let's go with that for now" …and hope they increase it later. "I am prepared to walk away" …if we can find a local replacement and if we have time.
4. Prefer "I cannot tell" to a confident attribution. You will be forgiven for asking. You will not be forgiven for putting words in someone's mouth in a document they read.

Three measured exemplars, from one correspondent in six days

The lesson from the third row is the one to keep. Finding the bug is not the same as fixing the model. The first reading trusted markers and missed 9 of 22 segments; the corrected reading trusted colour and would have missed the migration date. Only the nested model survives both.

Red flags — stop and verify by hand

• The sender describes a convention that your parser cannot find (says "in blue", no colour detected).
• Coloured-run count and marker count differ — the difference is unmarked continuation text, and continuations are where the conditions live.
• Colour appears in text/html but the matching text is absent from text/plain, or vice versa. Parse both parts and take the union; never prefer one. Clients generate them independently, so offsets from one do not map onto the other.
• More than two apparent authors in a two-party thread — usually one author split across colour spellings (blue / #00F / rgb(0,0,255)), which is why colour must be normalised to a canonical triple before any equality test.
• Any CJK full-width punctuation (＞＞, ：, 【PT】). ^> does not match ＞, so a full-width-quoted thread parses as 100% new text by the last replier.

Before the archive, not after

Colour lives only in text/html. An archive that stores text/plain alone cannot answer "who said what" later — the evidence is simply not in it, and you will find yourself back at the API to answer a question your own records should have settled. Store both parts. read --json returns plain text only; fetch format=full for the html:

curl -s --noproxy '*' -H "Authorization: Bearer $TOK" \
  "https://gmail.googleapis.com/gmail/v1/users/me/messages/<id>?format=full" \
  | jq -r '[ .. | objects | select(.mimeType? == "text/html") | .body.data ]
           | map(select(. != null)) | .[0] // empty' \
  | tr '_-' '/+' | base64 -d > msg.html

And never strip quoted history when a sender replies inline — their answers live inside the quotes, so stripping deletes the reply and keeps the signature.

The full catalogue

Normalisation that must precede every rule (quoted-printable, format=flowed, CRLF, colour canonicalisation, entity decoding, NFKC, Word conditional comments), per-client priors, typed-marker regexes, and the client artifacts that masquerade as authorship signals: references/attribution-parsing.md.

Inline Image Extraction

Emails often contain copy-pasted screenshots (inline images embedded in the HTML body, not file attachments). These appear as [image: image.png] placeholders in plain text but contain real image data accessible via the Gmail API.

Key Behavior

Output Sections (when images are present)

--- Inline Images (3) ---
  image.png   image/png   245.3 KB
  image.png   image/png   512.1 KB
  photo.jpg   image/jpeg  89.7 KB

--- Saved to Disk ---
  ./attachments/01_image.png  (251,234 B)
  ./attachments/02_image.png  (524,001 B)
  ./attachments/03_photo.jpg  (91,852 B)

--- Markdown References ---
![01_image.png](./attachments/01_image.png)
![02_image.png](./attachments/02_image.png)
![03_photo.jpg](./attachments/03_photo.jpg)

Important: Inline Images vs File Attachments

These are two disjoint channels, surfaced and downloaded separately:

A plain gmail read <id> (no flags) shows both as metadata blocks (filename, MIME, size) without downloading — so you can see a PDF exists before pulling it. export and read --json both carry attachments[] (and inlineImages[]) in their JSON.

has:attachment matches real file attachments but NOT inline images. Gmail search has no operator for inline images. To discover emails with inline images, you must read the email and check the MIME tree.

Strategy for finding emails with inline images:

# Search by sender/date, then read each to check for images
$GMAIL_CLI search "from:sender@example.com after:2026/02/01" -n 10 --json | \
  jq -r '.[].id' | while read id; do
    COUNT=$($GMAIL_CLI read "$id" --json | jq '.inlineImages | length')
    [ "$COUNT" -gt 0 ] && echo "$id has $COUNT inline image(s)"
  done

Gmail Threading and Image Deduplication

When downloading images from a thread (multiple reply emails), later replies include all prior inline images. The last email in a thread is typically the superset.

Recommendation: For threaded conversations, download images from the latest reply only to avoid duplicates. Compare by file size if unsure.

Filename Collision Handling

Copy-pasted screenshots often all share the generic filename image.png. The CLI prefixes a zero-padded index: 01_image.png, 02_image.png, etc. These machine-generated names should be renamed to descriptive names for correspondence archival.

Post-Download: Annotation Transcription Protocol

When inline images contain handwritten annotations (circles, arrows, written text overlaid on screenshots), perform a systematic two-level analysis:

1. Scene description: What does the screenshot show? (e.g., "Career portal main page showing position listings")
2. Annotation inventory: Exhaustively catalog every non-original markup element:
   • Hand-drawn shapes: circles, ovals, arrows, underlines, crosses — note what they encompass
   • Handwritten text: transcribe verbatim in quotes, note legibility and location on the image
   • Typed test inputs: text entered into form fields visible in the screenshot
   • Highlights or color markings: note color and what is highlighted

Format annotations as blockquote captions beneath each image in markdown:

![Scene description — annotation summary](path/to/image.png)

> **Annotation transcription**: [Detailed description of visual markup.]
> Handwritten text reads: _"exact transcription here"_
> [Interpretation of what the annotator is requesting.]

Do NOT defer annotation transcription to a second pass. Capture all annotations on the first image examination to avoid redundant re-reads.

File Attachment Extraction

Real file attachments (PDF, docx, csv, …) are surfaced in attachments[] and downloaded with --save-attachments / --attachment-dir. Same fetch path as inline images, different metadata field.

# See what a message carries (no download) — both metadata blocks print
$GMAIL_CLI read <id>          # → "--- Attachments (1) ---  foo.pdf  application/pdf  192.5 KB"

# Download to a chosen dir; files are index-prefixed + sanitized
$GMAIL_CLI read <id> --attachment-dir ./files/

# Discover which messages in a corpus actually carry attachments
$GMAIL_CLI search "from:sender@example.com has:attachment" -n 20 --json | \
  jq -r '.[].id' | while IFS= read -r id; do
    N=$($GMAIL_CLI read "$id" --json | jq '.attachments | length')
    [ "$N" -gt 0 ] && echo "$id → $N attachment(s)"
  done

Why this matters for archival: in clinical/legal/operational mail the attached PDF (a protocol, a vendor form, a signed consent) is often the most important payload. A body-only export silently loses it. Always check attachments[] when archiving a correspondence thread.

Bulk Retrieval & Thread Archival

The canonical pattern for archiving a whole correspondence (verified on a 27-message, 15-thread clinical corpus):

1. Scope with high-signal queries, not generic keywords. A bare keyword ("Curve") returns mostly newsletter noise. Prefer:
   • domain: vendor-domain.com (matches from/to/cc on the org)
   • participant: from:someone@example.com OR to:…
   • project code: any internal tag the sender uses (e.g. 1233V)
2. Collect message IDs from search --json (snippet-only) and curate the in-scope set out of the noise.
3. Fetch full bodies with a read --json loop (one file per message).
4. Group by threadId client-side — Gmail's list/search APIs return individual messages, not threads; you reconstruct threads yourself.
5. Sort within a thread by parsed Date and strip quoted history (drop >-prefixed lines and everything after On … wrote:) to expose each message's new content.
6. Pull attachments for any message whose attachments[] is non-empty.

# Robust batch fetch. NOTE: in zsh `for id in $VAR` does NOT word-split —
# always loop with `while IFS= read -r` over newline-delimited IDs.
printf '%s\n' $IDS | while IFS= read -r id; do
  [ -n "$id" ] && $GMAIL_CLI read "$id" --json > "raw/$id.json"
done

export is the one-call shortcut (fixed)

gmail export -q "<query>" -o out.json -n N writes one JSON array with full body + inlineImages[] + attachments[] per message — the batch-fetch shortcut when a single query captures your set. (Historical note: before the fix, export printed "Exported N emails to <path>" but wrote no file — outputPath was an unused parameter. If you see that symptom, the binary is stale; rebuild it.) export does not download attachment bytes — it only carries the metadata; use read --save-attachments per message for the files.

Creating Draft Emails

The draft command creates emails in your Gmail Drafts folder for review before sending.

Required options:

• --to - Recipient email address
• --subject - Email subject line
• --body OR --body-file - Email body text (one of the two)

Optional:

• --body-file - Read body from a file instead of --body. Useful for multi-paragraph bodies that are awkward to pass on the shell. Mutually exclusive with --body; if both are passed, --body wins with a stderr warning.
• --attach - File path to attach. Repeatable for multiple attachments. MIME type is guessed from extension (PDF, PNG, JPEG, DOCX, XLSX, ZIP, MD, JSON, etc. → mapped; unknown → application/octet-stream). Total message size ≤ 25 MB (Gmail limit; the CLI surfaces a 413 with a helpful hint if you exceed it).
• --from - Sender email alias (auto-detected when replying, see Sender Alignment below)
• --reply-to - Message ID to reply to (creates threaded reply with proper headers)
• --json - Output draft details as JSON

MANDATORY Sender Alignment (NON-NEGOTIABLE)

The user has multiple Send As aliases configured in Gmail. The From address MUST match correctly or the recipient sees a reply from the wrong identity.

Rule 1 - Replies (--reply-to is set): pass --from ANYWAY.

The CLI attempts to auto-detect the sender by reading the original email's To/Cc/Delivered-To headers and matching against the user's Send As aliases, and prints what it chose:

From: amonic@gmail.com (auto-detected from original email)

Do not trust that line to be the identity you want. Auto-detection resolves to the underlying account rather than the alias even when the original was addressed to the alias. Measured 2026-08-25: a message addressed to Ricky Chan <rickychanbc@gmail.com> produced From: amonic@gmail.com, silently, with no warning — and rickychanbc@gmail.com is an accepted send-as alias on that very account. The draft looked successful.

This matters because the alias IS the identity, not a cosmetic label. Where a correspondence policy says which name to sign as, the account and the alias are different signatories, and getting it wrong sends the whole message as the wrong person. Note also that the default alias on this account is terry@eonlabs.com, which policy forbids for non-Eon-Labs mail — so an omitted or mis-detected --from can reach for an identity that is not merely wrong but prohibited.

So: always pass --from explicitly, on replies as well as new mail, and read the confirmation line back before trusting it. If a draft was already created without it, draft-update <draftId> --from … recreates it correctly — it does not patch in place, so re-supply every other flag too.

There is no --cc flag. A reply draft therefore carries only To, even when the thread it replies into copied other people. Threading is preserved (In-Reply-To/References are set), but the copies are not. On a thread with a client and several vendors copied, this silently drops all of them from a reply sent on that client's behalf. Either restore the copies in the Gmail compose window before sending, or state plainly in your handoff that the CC list needs restoring — never let a draft go out assumed to be a reply-all.

Rule 2 - New emails (no --reply-to): When drafting a brand new email (not a reply), you MUST use AskUserQuestion to confirm which sender alias to use BEFORE creating the draft. Never assume the default.

AskUserQuestion({
  questions: [{
    question: "Which email address should this be sent from?",
    header: "Send As",
    options: [
      // Populate from known aliases or let user specify
      { label: "amonic@gmail.com", description: "Personal Gmail" },
      { label: "terry@eonlabs.com", description: "Work email" },
    ],
    multiSelect: false
  }]
})

Then pass the selected address via --from:

$GMAIL_CLI draft --to "recipient@example.com" --from "amonic@gmail.com" --subject "Hello" --body "Message"

Rule 3 - Always verify in output: After draft creation, confirm the From address is shown in the output. If it's missing or wrong, delete the draft and recreate.

MANDATORY Post-Draft Step (NON-NEGOTIABLE)

After EVERY draft creation, you MUST present the user with a direct Gmail link to review the draft. This is critical because drafts should always be visually confirmed before sending.

Always output this after creating a draft:

Draft created! Review it here:
  https://mail.google.com/mail/u/0/#drafts
From: <sender_address>

Never skip this step. The user must be able to click through to Gmail and visually verify the draft content, sender, recipients, and threading before sending.

Example: Reply to an email (auto-detected sender)

# 1. Find the message to reply to
$GMAIL_CLI search "from:someone@example.com subject:meeting" -n 5 --json

# 2. Create draft reply - From is auto-detected from original email's To header
$GMAIL_CLI draft \
  --to "someone@example.com" \
  --subject "Re: Meeting tomorrow" \
  --body "Thanks for the update. I'll be there at 2pm." \
  --reply-to "19c1e6a97124aed8"

# 3. ALWAYS present the review link + From address to user

Example: New email (must ask user for sender)

# 1. Ask user which alias to send from (AskUserQuestion)
# 2. Create draft with explicit --from
$GMAIL_CLI draft \
  --to "someone@example.com" \
  --from "amonic@gmail.com" \
  --subject "Hello" \
  --body "Message body"

# 3. ALWAYS present the review link + From address to user

Note: After creating drafts, users need to re-authenticate if they previously only had read access. The CLI will prompt for OAuth consent to add the gmail.compose scope.

Gmail Search Syntax

Reference: https://support.google.com/mail/answer/7190

Environment Variables

Proxy Auto-Bypass for Google API Hosts

If HTTPS_PROXY (or HTTP_PROXY) is set in the environment, the CLI automatically injects the following hosts into NO_PROXY at module load — before any auth or API call is made:

• .googleapis.com (covers gmail.googleapis.com, oauth2.googleapis.com, etc.)
• .google.com
• accounts.google.com
• oauth2.googleapis.com

Why this exists: many corporate networks (Cloudflare WARP, mitmproxy local interceptors, ITP-style local proxies) can't tunnel CONNECT to Google API hosts. When the proxy fails, the response surface returns HTTP 502 with an empty error body — the googleapis library throws a gaxios error whose .message is empty, which used to render as a useless empty Error: in stderr.

By force-bypassing the proxy for Google hosts, end-users with a corporate proxy can run the CLI without manually setting NO_PROXY or unsetting HTTPS_PROXY per-command.

Idempotent: the injection only adds entries that aren't already present in NO_PROXY. If you've manually configured NO_PROXY=.googleapis.com, the CLI leaves it alone.

Diagnosing remaining proxy issues (rare): if you still see HTTP 5xx errors, the CLI's new error formatter prints the full URL + response body + a hint. Check that HTTPS_PROXY was set BEFORE the CLI started (env-var detection is one-shot at module load).

Error Messages

The CLI's top-level error handler renders unknown errors as structured messages with HTTP status, request URL, response body snippet, and a category-specific hint. Example for a 404 on a bogus draft ID:

Error: HTTP 404 Not Found DELETE https://gmail.googleapis.com/gmail/v1/users/me/drafts/r-doesnotexist123
  body: {"error":{"code":404,"message":"Requested entity was not found.",...}}
  hint: message / draft ID not found. List existing drafts with `gmail drafts` first.

Hint categories:

Network-layer errors (ECONNREFUSED, ENOTFOUND, etc.) are surfaced with their error code instead of the

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