Proposal Attachments let you upload files to a campaign — Lancer includes them automatically on every proposal it submits. Available to all organizations.
Fixed mode vs Smart mode
The Proposal Attachments section in your campaign's Automation tab has a Fixed / Smart toggle.
Fixed — the same set of files attaches to every proposal this campaign sends (e.g. a standard portfolio PDF or capability deck). This is the default.
Smart — you define up to 3 cases, each with a plain-language condition and its own files. For each bid, AI reads the job's title, description, and screening questions and attaches the files of whichever cases match.
Switching between modes preserves your files in both modes — nothing is deleted when you toggle.
Setting up Fixed attachments
Open your campaign and go to the Automation tab.
Scroll to the Proposal Attachments section and confirm the toggle is set to Fixed.
Click Add files and choose up to 5 files from your device.
Uploaded files appear in the list immediately and are stored securely.
Setting up Smart attachments
Set the toggle to Smart.
Click Add case. You can have up to 3 cases per campaign.
In the condition field, describe in plain language when these files should be attached — for example: "Client wants a Shopify or e-commerce store." or "Job mentions a mobile app (iOS/Android)."
Click Attach files inside the case card to add up to 5 files to that case.
Cases with an empty condition are skipped and highlighted with a red border — add a condition or remove the case.
How matching works: At bid time, AI reads the job's title, description, and screening questions and returns a yes/no decision for each case. Files from all matching cases are combined, deduplicated, and uploaded (up to 5 total, in case order). Your file contents are never sent to the AI — only your condition text and the job text are used.
Limits
Fixed mode: up to 5 files per campaign, 25 MB each.
Smart mode: up to 3 cases, up to 5 files per case, 25 MB each.
Per-proposal cap: at most 5 files are uploaded to any single proposal. If multiple Smart cases match and together exceed 5 files, only the first 5 (in case order) are uploaded.
Duplicate filenames are rejected — rename the file and try again.
Executable and script file types are blocked (e.g.
.exe,.bat,.jar,.vbs).
How attachments are sent
When Lancer submits a proposal, it downloads your files and uploads them through Upwork's proposal form before submitting.
Attachments are sent on a best-effort basis — if the upload to Upwork fails for any reason, Lancer still submits the proposal without the attachment rather than skipping the job entirely.
In Smart mode, if the AI matcher times out or errors, no files are attached for that bid (the proposal still submits).
Each file's size and checksum are verified after download to confirm it arrived intact.
Removing attachments
Click the trash icon next to any file to remove it.
Removal takes effect immediately — the file will not be attached to future proposals, but does not affect proposals already submitted.