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Attach files that prove you have done this kind of work before. The Attachments step holds the files a proposal from this template carries.
The Attachments step with a file sent with every proposal and three smart attachment cases
A template holds up to 10 files in total, 20 MB each. A larger file fails with ”… is larger than 20 MB. Upwork rejects attachments over 25 MB, so we cap files at 20 MB.” One file too many fails with “A proposal template can have at most 10 attachments. Remove a file to add another.” The Chrome extension uploads the files into the Upwork form one by one, in the order Vollna sends them. A file that fails to upload is skipped, and the proposal still goes out.

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Sent with every proposal

Put files here that fit every job you bid on, such as your CV or a portfolio deck.
Upwork scans every file before the proposal goes out:
  • Keep contact details out of every file. An email, a phone number or a link in a PDF, a slide, or a file inside an archive blocks the whole proposal.
  • Upwork drops unsupported files without a warning. Documents, images, video and archives work. Send an uncommon format with one proposal by hand before you rely on it here.
  • Executables and scripts, like .exe or .bat, are never accepted.

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Smart attachments

Smart attachments: the fintech case matches a Stripe payments job, so its files go out
Smart attachments send each file only to the jobs it proves. Your fintech case study goes to fintech jobs, your Shopify store to Shopify jobs. The AI reads the job when it writes the letter, and attaches the files of the case that fits.
  • Smart attachments (default off): the switch for the whole section.
  • When a job matches several cases (default Attach the best match): Attach the best match compares every case and attaches the one that fits best. A case such as “any other job” then works as a fallback. Attach every match sends the files of every matching case, so write each condition to stand on its own.
  • Case (up to 10 per template): one kind of job and its files.
  • Describe when to send these (required for a case with files, up to 1,000 characters): the condition. Without it, the step shows “Describe when to send the files in each case” and Save stops.
A case fits only when the job meets everything its condition asks for. When no case fits, the proposal carries only your “Sent with every proposal” files. When a case fits, its files go first, then the files sent with every proposal. Describe the job in the condition. “The client runs a Shopify store or wants one built” picks better than “Shopify portfolio”. Turning smart attachments off keeps your cases and their files saved. The step shows how many case files are on hold: “1 file in your cases is not sent while smart attachments are off.”

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Check it on a real job

Preview on a real job opens the Attachments preview. Pick a job and click Check attachments. The preview shows the files the proposal would carry and the AI’s reasoning. Green means a case matched. Yellow means none did. The check uses your unsaved cases, so test a condition before you save it. It writes no letter and uses no AI credits.
Attachments preview: Case 1 matches a Stripe payments job and attaches its two files plus the portfolio