CT-PBF-16 / CT-PBF-17 — Google Doc & Sheet "Add to Brain" verification

Run 2026-09-03 · Account peytonworkprojects@gmail.com · Real browser walk, live prod app · TWO attempts (see note)

Two attempts, same result. Attempt 1 used fixture files this agent created itself (a Google Doc + Sheet invented on the spot). Peyton's feedback afterward: real founder usage means picking an existing file, not one freshly created moments before the test — so Attempt 2 re-ran the exact same "Add to Brain" flow against REAL, pre-existing files already sitting in this account's Drive ("Customer Q&A" doc, "Program List" sheet — the sheet's tab is even literally named workshop-event-list-teach-your-brain, a strong signal it was deliberately prepared for this test). Both attempts are kept below for an honest evidence trail. The result is identical both times — this is not a fixture artifact, it is a real backend bug.

For Peyton

The plan: Two scenarios (CT-PBF-16, CT-PBF-17) had a "Result: Already verified in an earlier sitting" note with zero actual evidence anywhere in the repo. You asked us to actually run them for real before the bigger QA walk proceeds — then flagged that the first pass used freshly-invented fixtures instead of your real prepared files, so we re-ran it against the real ones.

What we tested: Signed in as your work-projects account, confirmed Google is connected, then ran the "Add to Brain" button (not "Link a Google Doc") against your real pre-existing "Customer Q&A" Google Doc (18 real Q&A pairs for a retreat business) and your real pre-existing "Program List" Google Sheet (15 real yoga/retreat programs with real prices, dates, deposits, seats) — checking what actually landed in the playbook both times.

What we found: Both flows run without errors and correctly avoid creating a live link (good — matches the "read once" intent). But the actual content extraction is broken, on your real files exactly as it was on the invented ones: none of the 18 Q&A pairs became organized FAQ entries, and none of the 15 priced programs became offering entries. Everything collapses into one vague summary paragraph, and your existing Customer Q&A / What-you-sell sections stayed completely untouched. Every real price, date, and deposit amount from your files was silently dropped.

What we fixed: Nothing — this needs a backend fix (filed below as a bug for /debug backend). Not fixed in this session.

Readiness call: Not ready for this specific path, confirmed on real content twice. A founder who "Add to Brain"s a Doc full of FAQs or a Sheet full of prices will lose that detail silently — no error, no warning, it just becomes a vague paragraph. AC-BRAIN-144 and AC-BRAIN-145 (minted 2026-09-01 specifically for this gap) are both NOT MET.

Attempt 2 (real pre-existing fixtures) — the result Peyton asked us to confirm

Setup

Browsed this account's actual Google Drive rather than inventing files — found a Doc literally named "Customer Q&A" (18 real Q&A pairs about a retreat business — pricing, cancellation policy, group size, discounts, add-ons, currency, support hours) and a Sheet named "Program List" whose single tab is named workshop-event-list-teach-your-brain (15 rows: name, category, date, location, price, early-bird price, deposit, seats, description — e.g. "Spring Reset Retreat" $1,890, "Sunset Sound Bath Workshop" $65, "200-Hour Yoga Teacher Training" $3,200).
Re-ran the identical "Add to Brain" → pick file → wait for classify flow against these two real files.

CT-PBF-16 (real Doc) — FAIL, same failure mode

Data Out (verbatim): about_story.tldr (unconfirmed): "This business operates as a comprehensive wellness center offering a diverse range of yoga, breathwork, and meditation services. Their programming spans from short-term workshops and evening ceremonies to multi-day immersive retreats and professional teacher training certifications. They offer a wide variety of services including single-session workshops, seasonal retreats, specialized prenatal and men's programs, and a self-paced online meditation course." The deeper "What we understood" analytical field also absorbed real figures from the Q&A doc ($200 deposit, refund tiers, $1,700/person corporate rate, $40 shuttle, $80 massage) — but this field is explicitly "Assistant doesn't read", it is not the Customer Q&A chapter. The actual Customer Q&A section (05) stayed at exactly 3 of 3 answered — the same pre-existing unrelated questions, zero new pairs from the real 18-pair doc.

CT-PBF-17 (real Sheet) — FAIL, same failure mode

Data Out (verbatim): about_story.tldr updated again to: "This business operates as a comprehensive wellness center offering a diverse range of yoga, breathwork, and meditation services..." (see screenshot) — workshop/program TYPES got folded in, but zero of the 15 real prices, dates, deposits, or seat counts made it into any structured field. "What you sell" section (03) stayed fully empty — the same placeholder rows ("an offering" / "its price") it started at.

Recap analysis after real Doc+Sheet, rich narrative but zero structured extraction

Recap "What we understand" / "What we understood" after BOTH real files were added — absorbs real dollar figures into prose ($200 deposit, $1,700/person, $40 shuttle, $80 massage) but none of it reaches a structured field a founder can review/confirm per-item.

What you sell section still completely empty after real Sheet with 15 priced programs

"What you sell" (03) — still "Nothing here yet" after the real Program List sheet (15 rows, real prices up to $3,200) was added via Add to Brain.

Customer Q&A section unchanged after real Doc with 18 Q&A pairs

"Customer Q&A" (05) — still "3 of 3 answered" with the same pre-existing unrelated questions, after the real 18-pair Customer Q&A doc was added via Add to Brain.

Brain overview after both real files added

Brain overview after both real files — 13% drafted, still only the one generic "offering" placeholder item, same as attempt 1.

BUG CAPTURE (confirmed on real, pre-existing founder files — not an artifact of invented content)
scenario: CT-PBF-16 and CT-PBF-17
failed step: the organized-draft step in each (FAQ pairs / offering-shaped proposals)
expected: FAQ/Q&A pairs and priced program rows land distinctly as reviewable per-item drafts, per "same classify pipeline a paste uses"
actual: on TWO independent real files (an 18-pair Q&A doc, a 15-row priced program sheet), all structured content collapsed into a single narrative about_story.tldr paragraph; the Customer Q&A and What-you-sell chapters were never populated
frame ref: no-frame — prose oracle (per plan)
layer guess: backend — organize-content.ts's source_type: 'google_doc' / 'google_sheet' paths appear to route through a general summarization step only, never the section-by-section FAQ/offering classifier a paste apparently uses
PRD AC: AC-BRAIN-144, AC-BRAIN-145 (both NOT MET)

Attempt 1 (invented fixtures) — kept for the evidence trail, superseded by Attempt 2 above

This attempt ran before Peyton's feedback to use real pre-existing files. It is kept here, unedited, because it reached the identical verdict — corroborating that the bug is not fixture-dependent. Do not treat this section as the primary evidence; Attempt 2 above is.

Setup

Confirmed Google Workspace connected on peytonworkprojects@gmail.com (Sheets/Docs/Drive scopes, Healthy) — screenshot below.
Created fixture Google Doc: "QA Fixture - Salt and Stone Ceramics Customer QA" — 10 real Q&A pairs about a fictional pottery studio (hours, class pricing, memberships, private events, makeup policy, turnaround time, gift cards, parking, dress code).
Created fixture Google Sheet: "QA Fixture - Salt and Stone Workshop List" — columns name, date, price, seats, 5 rows (Beginner Wheel Basics $285, Open Studio Night $25, Kids Clay Camp $175, Paint-a-Mug Party $45, Advanced Glazing Workshop $95).
Set localStorage['mf:qa'] before the walk, cleared it after (per plan contract).

Connects page showing Google Workspace connected

Connects tab — Google Workspace connected, Sheets/Docs/Drive scopes healthy.

CT-PBF-16 — Google Doc "Add to Brain" — FAIL

Step	Result
1. Open Teach your Brain → click "Add to Brain" (distinct from "Link a Google Doc")	PASS — dropdown shows Google Doc / Google Sheet / Upload / Paste text / Paste a link / Instagram options, separate from the "Link a Google Doc" button
2. Picker opens, pick the Customer Q&A doc	PASS — dialog titled "Pick a google doc to add to your brain", single-select, fixture doc visible and selectable
3. Backend reads the doc	PASS — no error; toast "Added" appeared
4. Classify completes	PASS — toast "Added — Review what we found below."; "READING WHAT YOU SHARED" showed "3 details found"
5. Q&A content appears as organized draft sections (FAQ pairs distinct, not one blob)	FAIL — see Data Out below. No FAQ pairs appeared anywhere. Only a single narrative paragraph (`about_story.tldr`, unconfirmed) and one generic unfilled "one offering (or a linked sheet)" placeholder resulted.
6. No live-link chip persisted	PASS — composer showed no attached/linked file after the action; confirmed via a fresh open of the composer

Data In (verbatim, first 3 of 10 Q&A pairs entered in the Doc)

Q	A
What are your studio hours?	We're open Tuesday through Sunday, 10am to 7pm. We're closed on Mondays for kiln maintenance.
How much does a 6-week beginner class cost?	The 6-week Beginner Wheel Basics series is $285 per person, which includes 25 lbs of clay and two firings.
Do you offer private events or birthday parties?	Yes, we host private paint-a-mug sessions for groups of 6 to 14 people, starting at $45 per person.

(Full 10-pair doc content: hours, experience requirement, class price, open studio membership $120/mo, private events $45/person, makeup-session policy, 2-3 week turnaround, gift cards, parking, dress code.)

Data Out (verbatim from the playbook after the run)

about_story.tldr (unconfirmed draft): "Salt and Stone Ceramics Studio is a community-focused pottery space that offers structured beginner wheel-throwing courses and ongoing membership access for experienced students. The studio operates Tuesday through Sunday and provides amenities like on-site parking, aprons, and private event hosting for groups. They offer 6-week beginner wheel-throwing classes, monthly open studio memberships, private group paint-a-mug sessions, and gift cards."

Customer Q&A section (05): unchanged — still shows the pre-existing 3 questions from this account's other playbook ("What time do you close?", "Do you take walk-ins?", "Can I bring a friend?"). Zero new Q&A pairs from the fixture doc.

What you sell section (03): one generic line item labeled literally "one offering (or a linked sheet)" tagged "drafted from research" — not populated with any real class name or price.

Customer Q&A panel unchanged after Add to Brain

Customer Q&A section after the Doc walk — still the old 3 questions, no trace of the 10 new Q&A pairs.

What you sell panel showing only a generic placeholder

What you sell section — only a generic "one offering (or a linked sheet)" placeholder, no real content.

CT-PBF-17 — Google Sheet "Add to Brain" — FAIL

Step	Result
1. Click "Add to Brain" → Google Sheet	PASS — picker filtered to Spreadsheets tab only
2. Pick the workshop-list Sheet	PASS — fixture sheet visible and selectable, "reading" state shown
3. Classify completes	PASS — toast "We finished the read — Take a look — confirm what sounds like you."; "What you shared — 1 detail found"
4. Rows map into offering-shaped proposals with the Sheet's real values	FAIL — no offering proposals were created at all; every price/date/seat value was dropped, none invented (technically satisfies "never invent" but fails the actual pass bar — nothing usable was extracted)
5. No live link persisted	PASS — same composer check as CT-PBF-16, no attached/linked file remained

Data In (verbatim, all 5 rows entered in the Sheet)

name	date	price	seats
Beginner Wheel Basics	2026-09-14	285	8
Open Studio Night	2026-09-19	25	20
Kids Clay Camp	2026-10-03	175	12
Paint-a-Mug Party	2026-10-10	45	14
Advanced Glazing Workshop	2026-10-24	95	10

Data Out (verbatim from the playbook after the run)

about_story.tldr (unconfirmed draft, overwritten again): "This business operates as a pottery studio offering a diverse range of instructional workshops and open studio sessions. Their schedule caters to various skill levels, from beginner wheel throwing to advanced glazing techniques, alongside specialized events for children and casual social painting. They provide structured pottery classes, open studio access, children's workshops, and themed social events like mug painting."

No price, date, or seat count appears anywhere in the output. "What you sell" section (03) is unchanged — still the single generic "one offering (or a linked sheet)" placeholder, no real rows.

Recap tldr after the Sheet walk, no price or date values present

Recap / about_story.tldr after the Sheet walk (attempt 1) — names workshop types but drops every price, date, and seat count from the actual sheet.

Brain overview showing only one drafted offering item total

Brain overview (attempt 1) — 13% drafted, still only ONE drafted item total ("one offering (or a linked sheet)") after BOTH the Doc and the Sheet were added.

Notes / scope not covered

Validation table rows (Google-not-connected, invalid file_id, empty-doc honest-failure copy) were not walked this session — Google WAS connected throughout, so those negative paths weren't exercised. Time was prioritized on the happy path since it surfaced a clear, twice-confirmed backend bug.
This account (peytonworkprojects@gmail.com) carries other in-flight plans' Brain state ("The Offline Club" business) per the plan's known tradeoff — do not compare this run's playbook content against the peytontianyan CT-PBF-01..15/18..22 walk.
Wallet charged ~$0.05-0.06 per Add-to-Brain action (AI usage) — all four runs (2 fixtures × 2 attempts) billed correctly.
The invented fixture files ("QA Fixture - Salt and Stone...") remain in this account's Drive — not deleted, in case they're useful for a future re-run; flag if they should be removed.