Troubleshooting

Personal Outlook accounts (@outlook.com, @hotmail.com, @live.com) can't connect at all. Brokerage accounts may need IT approval, and some brokerages block outside apps. Skip the email search and use Route A, B, or C. Uploads work with nothing connected.

• Forwarded mail only starts the day forwarding was turned on, and only includes what came in, not what you sent.
• Check Spam, Archive, and any labels where forwarded mail lands.
• Give Claude more names: every title company, escrow officer, and TC you've worked with.
• The details may be in attachments Claude can't open. Download those closing statements and use Route B.

Tell it exactly what's wrong and have it fix the file: "Jane Smith is the escrow officer on 123 Main St, not my client. Remove her, find my actual client, and update the file." Then check your "Likely" contacts from Step 1. A missed lender or escrow officer usually shows up there.

Tell it who's who: "John and Mary Lee are two people who share an email. Keep them as separate rows."

Start a fresh chat, upload the files you have so far, and pick up where you left off. That's why it's one year per chat.

Wait for it to reset, or work in smaller batches: fewer files per upload, one year at a time. A paid plan gives you more room.

Upload your CRM's import template and ask Claude to match its columns and date format exactly. Most errors are column names or date formats.

Most personal Messenger chats are end-to-end encrypted and come from a separate download. See Bonus 2: Messenger's newer chats.