◈ Observify

This page already confirms the whole diagnosis in writing: no Return Transcripts exist at all — instead the IRS offers you Verification of Non-Filing letters for 2022–2025 (those PDFs are literally official proof of what you told me: nothing filed). Account transcripts exist only for the four stimulus/inquiry years we already understand. The panel that matters now is Wage & Income — it's showing 2022–2025, but there's a "Show more transcripts" link at its bottom right, and wage & income records typically go back about 10 years.

Step 5 of ~8 — expand the Wage & Income list.

Click "Show more transcripts" at the bottom of the Wage & Income Transcripts box.

Send me: a screenshot of the expanded list — I need the oldest year it offers. That single fact decides how much of your work history we can pull from the IRS directly (likely back to ~2016) versus what we'll need the Social Security earnings record for (everything older).

Ten years on offer — 2016 through 2025. Everything older than 2016 will come from the SSA later; this is as deep as the IRS window goes, and it's plenty for the catch-up (remember: they generally want six years).

Step 6 of ~8 — harvest the documents.

Two download runs on this same page, saving everything into one folder (make a taxes-catchup folder somewhere you'll find it):

1. In the Wage & Income Transcripts box: click the EN link next to each year, 2016 through 2025 — ten PDFs. Each opens in a tab; save it (⌘S) named by its year.
2. Scroll up to the Account Transcripts box and do the same for 2020–2023 — four more PDFs. These are your written proof that nothing was ever assessed; whichever firm you hire will ask for exactly these.

Don't paste the PDFs into this chat — they carry income figures and partial identifiers. Instead, skim each Wage & Income PDF: it's a per-year list of every form filed under your SSN, grouped by payer ("Form W-2 — [employer]", "Form 1099-NEC — [payer]", etc.).

Send me a simple per-year tally, like: 2019: 2 W-2s, 1 1099-NEC · 2018: 1 W-2 · 2016: none. Include any form type you see — W-2, 1099-NEC/MISC/K/B/INT/DIV, 1098, 5498. Two of these matter beyond taxes: a 5498 is an IRA/retirement account custodian reporting — that's your lost-401(k) trail lighting up — and on any W-2, glance at Box 12 for a code "D", which means you were contributing to a 401(k) at that employer. Note which employers show a code D.

That tally is the gate: it tells us the real shape of the catch-up (how many states, how much 1099 income, which years actually owe vs. refund) — and it's the exact document set a CPA will quote from.

The files are on your local disk now — that's a surface I can drive, so instead of making you skim 14 PDFs, I'll read them and build the tally myself. Let me confirm the folder first.

While the extraction runs, we can knock out the loose end from the very first screen — the IRS can't mail you anything right now, and we should see what they've already tried to send.

Step 7 of ~8 — read your notice history, then we'll fix the address.

In the dark blue navigation bar, click "Notices and letters."

You should get a list (possibly digital copies) of notices the IRS has issued to you — I expect at least the "please file your 2023 return" letter (typically labeled CP59 or CP516/CP518) that the account-balance page referenced.

Send me: a screenshot of the list — the notice codes and dates are what I need, not the letter contents. If it's empty or says notices aren't available online, just tell me that; paper-only history is common and not a problem.

Two letters. That's the IRS's entire correspondence with you across 15 years — a "return not filed" nudge in December 2024 and a follow-up in December 2025, both about the missing recent return. No collection notices, no assessment letters, nothing with a dollar sign. The record fully supports the clean-slate picture.

Now let's make you reachable, so the eventual catch-up filings don't generate mail into the void.

Step 8 of ~8 (on this site) — fix the address and turn on email alerts.

Click the "View your profile" link right there in the "Manage your paperless or email notification preferences" paragraph.

On the profile page you'll find your mailing address on file (presumably years stale) with an option to update it, and toggles for email notifications / paperless. Update the address to where you actually live, and switch email notifications on — from then on, anything new lands in your inbox instead of a dead mailbox.

Send me: no screenshot needed for this one (it's all personal info) — just tell me two things: "address updated" and "email notifications on." If the site says address changes are processed with a delay or asks you to file a form instead, tell me what it says.

The extraction is back — before I present it, let me spot-check it against a raw PDF myself.

The extraction is done — I line-checked the 2023 transcript against the raw PDF myself and it matches exactly, so I trust the set. Here's what a decade of IRS records says about you, and it rewrites part of my earlier reassurance, so read this one carefully.

Your reconstructed work history (the thing you couldn't remember)

| Years | Employer (as filed) | Wages | 401(k)? |
|---|---|---|---|
| 2016–2018 | Philadelphia Academy Charter School (+ side 1099s ~$2–6k/yr from Phila. Education Partnership) | $33k → $55k → $37k | no |
| 2018 | Robert Half + "3 Data" (brief stints) | ~$1k | no |
| 2019–2020 | Trinity H III Inc | $70k, $65k | no |
| 2020–2021 | Mobile Programming LLC | $21k, $15k | no |
| 2021–2022 | Armstrong World Industries | $114k, $64k | yes — $9.2k deferred |
| 2022–2023 | Google | $127k, $204k | yes — $21.5k deferred |
| 2024–2025 | Cali Heal Inc (current) | $51k, $81k | yes — small, active |

The 401(k) mystery is mostly solved, and not the way we hoped: the transcripts show you already cashed the old ones out — Vanguard (Google's plan) paid you $32,822 in 2023, Fidelity + Vanguard paid $10,181 in 2024, another record-keeper $1,692 in 2025, all coded "early distribution," plus a small $2,378 cashout back in 2016. There's likely little left to hunt except anything pre-2016 (SSA record can confirm) and two small HSAs at Fidelity and HealthEquity (~$1–2.5k combined) that are still yours.

The money picture, year by year (rough math — the CPA does the real version)

• 2016–2021: withholding roughly covered your tax each year. Those refunds are forfeited, but there's also no meaningful debt hiding there.
• 2022 — problem year. Google withheld only $3,725 on $127k of wages (a payroll-election artifact). Roughly $15–20k owed, growing with penalties and interest since April 2023.
• 2023 — the big one. $204k salary + the $32.8k 401(k) cashout (which also carries a 10% early-withdrawal penalty) + stock sales + unemployment. Withholding fell well short: roughly $20–25k owed before late penalties. This is why the IRS started writing to you in Dec 2024 — they ran this same math.
• 2024 — money on the table. Modest income, heavy withholding: roughly a $3k refund, claimable until April 2028 but only by filing.
• 2025: the $19k 1099 from "Turi Ente In" has no withholding — call it $3–4k owed, small penalties so far since the deadline just passed in April.

So the honest revision of what I told you earlier: the old years are clean, but 2022–2023 carry a real five-figure combined balance, and the IRS is actively nudging on 2023 — if it stays unfiled, their next move eventually is filing it for you at the worst possible math. That's the urgency in this whole exercise, and it's also completely handleable: file the six years 2020–2025, take the 2024 refund against the pile, and set up an installment agreement on the rest (streamlined approval typically available at these balance levels). Penalty abatement is worth requesting given your otherwise-empty collection history.

One anomaly I need you to answer: New Jersey issued you a $524 refund for tax year 2022 — which means a 2022 NJ state return was filed. Did you (or someone — a preparer, a parent, TurboTax autopilot) file state returns some years even though federal never went in? Also: your state trail reads NJ → California → North Carolina. Which state are you actually in now? That sets how many state returns the catch-up needs.

Still open from the walkthrough: your address update + email notifications ("done/done" is all I need), and the four Account Transcript PDFs (2020–2023) into the same folder. Then the last step is the quote request — and you're now in a far stronger position than "15 years unfiled": the real engagement is six years, mostly W-2, two balance years, documents already in hand, which is a package any resolution CPA can price tightly.