Before you start
- Use a business plan. Claude Team, not Pro. Pro runs on consumer terms. Why that matters, and what it costs a solo.
- Your email and files should be business accounts too. Connecting a personal gmail.com inbox to Claude Team still leaves the email itself on consumer terms. Google Workspace and Dropbox's business plans are the matching pair.
- Read any protective order first. If discovery came with one, check whether it limits who and what can process the material.
Set it up
When you buy Claude Team, you're the account owner. That means two jobs: turn the connectors on for the account, then connect your own email and Dropbox.
- Turn the connectors on. In Claude, open Organization settings, then Connectors, then Browse connectors. Pick Gmail and click Add to your team. Do the same for Dropbox.
- Make Claude ask before it sends anything. The Gmail connector can send, reply and forward, not just draft. Under Tool permissions for Gmail, set send, reply and forward to Needs approval, or Blocked if you only want drafts.
- Connect your accounts. In a chat, click the + at the lower left, then Connectors, then Manage connectors. Click Gmail, then Connect, and sign in with your Workspace account. Then Dropbox: sign in and approve its permissions.
- If Google says "Access blocked": your Workspace has to trust Claude first. In admin.google.com go to Security, then Access and data control, then API controls, then Manage third-party app access. Find Claude, set it to Trusted, and give it about 15 minutes.
- Switch them on per chat. Click +, hover Connectors, and toggle Gmail and Dropbox on for the chat you're in.
Stuck on a step, or not sure how to ask for something? Ask Claude. It will walk you through its own settings, and if you describe what you want from a case file, it will write a better prompt than most of us would.
What each one can see
- Gmail searches and reads your email, and drafts replies. It sees that an email has an attachment but can't open it. Discovery that arrives as a PDF attachment needs saving to Dropbox before Claude can read it.
- Dropbox finds and opens files in your folders, and can organize them. It works within your existing Dropbox permissions.
- Uploading a PDF straight into a chat works for files up to 500MB. Claude reads up to 100 pages fully, including scanned pages. From 101 to 1,000 pages it reads the text layer only, so a long scanned transcript can come back nearly blank. Split it into pieces under 100 pages.
Anthropic says it doesn't train on Gmail or Drive connector data, and on Team nothing you do is used for training by default. What Claude pulls in through a connector is stored with the chat, so deleting the chat deletes it.
One Project per case
A Project in Claude is a workspace with its own files and its own standing instructions. Make one for each case, so Claude never mixes up two clients and you don't re-explain the case every time.
In the Project's instructions, write down what you'd tell a new associate on day one:
Commonwealth v. Rivera, Suffolk Superior, 2684CR00412. I represent the defendant. Charges: armed robbery, assault and battery with a dangerous weapon. The ADA is Jordan Morrow. Discovery is Bates-stamped CW-0001 and up. The client's case file is in Dropbox under Cases/Rivera.
When you state a fact from a document, give the Bates number, or the page and line for transcripts. Quote word for word when I ask for a quote. If you can't find something, say so. Don't guess.
That last paragraph matters more than the rest. It's what makes the answers checkable.
Find the emails that matter
Discovery fights, plea offers and deadlines are scattered through months of email. With Gmail connected, ask for them by name and date.
Find every email between me and ADA Jordan Morrow about Rivera since the arraignment on March 3. List each one with the date, who sent it, and any deadline, offer or promise in it.
Did the Commonwealth ever answer my request for the 911 recording? Quote the email where they did.
What has the ADA said about a plea, in order? Quote each offer exactly.
Give it names, a docket number or a date range. "Emails about my robbery case" makes it guess. And treat the list as a head start, not a full search. If something you remember isn't on it, search your inbox yourself.
Summarize grand jury minutes
Put the minutes in the case's Dropbox folder or upload the PDF to the Project. Then work through them one witness at a time. A whole transcript at once gets you a vaguer summary.
List every witness in the grand jury minutes, with the pages where their testimony starts and ends.
Summarize Officer Kane's testimony in order. Give the page and line for every fact.
Everything any witness said about the time of the stop, with page and line, quoted.
Find where the statements don't line up
This is where it saves the most time. Claude can hold a police report, a grand jury transcript and a witness interview side by side and compare them line by line, which takes a person an afternoon.
Compare Officer Kane's police report with his grand jury testimony. Make a table: the topic, what the report says with the Bates number, what he told the grand jury with page and line, and whether they conflict.
Build a timeline of the night from every document in the folder. Where two sources give different times or a different order of events, flag it and cite both.
Compare my client's account in my intake notes with the police report. Where do they disagree?
The last one is for preparing your client, not for cross. You want to know where their story and the report part ways before the ADA does.
Check everything before it leaves your desk
Claude reads fast and is usually right, and when it's wrong it sounds exactly as sure as when it's right. Before a summary, a timeline or an inconsistency goes into a motion or a cross outline:
- Open the page it cited and read the line yourself.
- Ask it to quote, not paraphrase, anything you plan to rely on.
- Scanned PDFs are the weak spot. If a transcript is a photocopy of a photocopy, spot-check more.
- It can miss things. "I found no conflict" means it found none, not that there isn't one.
One more risk: email from outside
Every email in your inbox was written by someone else, and some of them weren't written for you. Text in an email or a file can be worded to steer an AI that reads it. Anthropic warns about this for every connector. It's why step 2 above matters: keep sending on approval, and read anything Claude proposes to send before you click yes. Research mode, the deep-search option under +, runs connector actions without asking each time, so keep sending blocked if you use it.
This guide covers how the tools work, not legal advice. Claude and its connectors change often. The pages linked below are the current word.