The Scenario
The accounts team closed a batch of 60 invoices last quarter. The signed PDFs are sitting in a shared drive folder. Someone built an Excel workbook mapping each PDF filename to its Chaser invoice ID — created it three weeks ago, handed it off, and then went on leave. The task sitting in the queue says: attach all 60 PDFs to their Chaser invoice records so the collection team can reference them without leaving the platform.
Nobody on the remaining team has done this before.
The bad version:
- Open Chaser, search for invoice ID from row 1, navigate to the invoice, find the attachments tab, click "Upload," locate the PDF in the shared drive, confirm, wait, repeat.
- On row 18, realize that the filename in the Excel workbook has a space in it that the Chaser upload UI doesn't handle correctly, and the attachment silently fails without an error message — you only discover this when you go back to verify.
- Get through 40 rows and decide to take a break, come back, and lose track of which rows you've already done because column C doesn't have a consistent status value — you added "done" for some, left others blank, and wrote "uploaded" for the last ten.
Sixty invoices at three minutes each is three hours of clicking. The person who built the workbook thought someone would automate this. Nobody did.
The Easy Way: One Prompt in SheetXAI
SheetXAI is an AI agent that lives inside your Excel workbook. It reads the mapping you already have — invoice ID in one column, file path in another — connects to Chaser through its built-in integration, and uploads each PDF to its matching invoice record. Status comes back into column C so you have a clean record of what succeeded.
With the mapping workbook open, send this prompt:
For each row in this workbook, upload the PDF at the path in column B to the Chaser invoice whose ID is in column A — write 'attached' in column C if the upload succeeds, or write the error message if it fails. Skip any row where column C already says 'attached'.
What You Get
- Column C: "attached" for every invoice where the PDF uploaded successfully
- Column C: The specific Chaser error message for any row that failed — malformed invoice ID, file not found, unsupported format — so you know exactly what to fix
- Any row that failed can be corrected and re-run; rows that already say "attached" are skipped automatically on subsequent runs
- A complete audit trail of the upload batch lives in the workbook, so the collection team can verify attachment status without logging into Chaser
What If the Data Is Not Quite Ready
Some PDF paths have trailing spaces in column B and the upload fails silently
Trim all values in column B before uploading. For each row in this workbook where column C is not 'attached', upload the PDF at the trimmed path in column B to the Chaser invoice in column A — write 'attached' into column C on success, or the error message on failure.
The file paths are relative and I need to prepend the base drive path before uploading
Prepend 'https://drive.example.com/invoices/' to each value in column B, then upload the resulting full URL to the Chaser invoice ID in column A for each row where column C is empty — write 'attached' or the error into column C.
Some rows have the same Chaser invoice ID appearing twice because of a duplicate in the source data
Deduplicate the rows in this workbook by the invoice ID in column A, keeping the first occurrence of each, then upload the PDF at the path in column B to the corresponding Chaser invoice — write 'attached' or the error into column C and write 'DUPLICATE SKIPPED' into column C for any row that was removed.
Trim paths, prepend the base URL, deduplicate by invoice ID, upload all PDFs, and mark status — one prompt
Trim all values in column B and prepend 'https://drive.example.com/invoices/' to each. Deduplicate rows by column A keeping the first occurrence and mark duplicates with 'DUPLICATE SKIPPED' in column C. For each remaining row where column C is empty, upload the PDF to the Chaser invoice in column A — write 'attached' on success or the error message on failure into column C.
The pattern: data cleanup — trimming, path construction, deduplication — goes in the same prompt as the upload. You don't fix the workbook manually and then run the upload as a separate step.
Try It
Get the 7-day free trial of SheetXAI and open the Excel workbook with your invoice ID to PDF mapping, then ask it to attach all 60 files to their Chaser records in one pass. For related reading, see how to audit your customer contact data or batch-upsert a weekly billing export using SheetXAI with Chaser.