iPhone and iPad
- Update the app
- Allow Photos access: Settings › Perplexity
- Download iCloud files to the device first
- Convert HEIC to JPG
- Try perplexity.ai in Safari
Most common fixes
Check size, format and your daily limit first
Most upload problems come down to three things. Size: Perplexity’s FAQ lists 25 MB per file. Format: PDFs, text, code and images are officially supported; convert HEIC, Pages, ZIP and old Office files first. Limit: the free plan allows about 3 uploads a day. Not those? Use the diagnosis below. Test a file first with our file checker.
Diagnose your upload problem
Answer up to four questions to get the fix for your situation.
Look up an error message
Type a few words from the message you see (wording varies by app and version).
Fix the file
Make a file smaller or compatible
Using tools already on your device. Only upload documents you’re allowed to share.
| Problem | Windows / Mac | iPhone / Android |
|---|---|---|
| PDF too large | Mac: Preview › File › Export › Quartz Filter “Reduce File Size”. Windows: re-export from the original app with smaller images, or “Print to PDF” only the pages you need. | Share only the pages you need, or re-export from the original app. |
| Too many pages | Print to PDF with a page range (e.g. 1–40), repeat for the next range. | Use your PDF app’s page selection to share a range. |
| HEIC photo | Mac: Preview › Export › JPEG. Windows: Photos app › Save as JPG. | iPhone: Settings › Camera › Formats › Most Compatible; or share as JPG. |
| Pages / Numbers / Keynote | File › Export To › PDF, Word, Excel or PowerPoint. | Share › Export › PDF or Office format. |
| Old .doc / .xls / .ppt | Open and Save As .docx, .xlsx or .pptx. | Open in the Office or Google app and save a copy. |
| ZIP / RAR | Extract, then upload the files inside. | Files app: tap the ZIP to extract. |
| Huge spreadsheet | Save only the sheet you need as CSV. | Export one sheet as CSV. |
Menu names can vary by app version. Prefer tools on your own device over unknown “free PDF compressor” websites for private documents.
Devices
Fixes by device
Android
- Update the app
- Allow files and media permission
- Download Drive files first
- Free up storage space
- Try perplexity.ai in Chrome
Web browser
- Hard refresh
- Drag the file onto the question box
- Try a private window
- Disable extensions or VPN
- Try another browser
Mac and Windows apps
- Update the app
- Allow file access if asked
- Close and reopen the app
- Compare with the website
- Reinstall if it keeps failing
Prevent
Prevent upload problems
Check before you uploadUse the file checker for size and format.
Prefer text-based PDFsExported PDFs read far better than photos of pages.
Upload what you needOne chapter or sheet beats a 500-page file.
Keep reusable files in a SpaceThey don’t expire like thread uploads.
Wait for “uploaded”Ask only once the file shows as complete.
Mention the file“Using the attached report…” keeps answers on it.
Limits from Perplexity’s file upload FAQ and Spaces help; some 2026 sources report different figures (example). Full details: file uploads: formats, limits and tips.
FAQ
File upload problem questions
Why won’t Perplexity upload my file?
The most common reasons are a file over the size limit (25 MB in Perplexity’s FAQ), an unsupported format such as HEIC or Pages, the free plan’s daily upload limit, a password-protected or damaged file, or a connection problem. The diagnosis tool on this page walks you to the right fix.
What is the maximum file size for Perplexity uploads?
Perplexity’s FAQ says files are limited to 25 MB. Its Spaces help center lists up to 50 MB per file for paid users in Spaces, and some 2026 guides report about 40 MB in regular threads.
How many files can I upload on Perplexity Free?
Perplexity’s FAQ lists up to 3 file uploads a day on the free plan, and unlimited (at least 100) on Pro.
Why does Perplexity ignore my uploaded file?
It may not have finished uploading, your question may not refer to it, or the file may have expired from the thread. Say “Using the attached file…”, re-attach it if needed, or keep it in a Space.
Why can’t Perplexity read my PDF properly?
Scanned pages, handwriting, low-quality photos and complex tables are harder to read. Use a text-based PDF where possible, upload the pages that matter, and ask for page numbers so you can check.
Can I upload HEIC photos from my iPhone?
HEIC may not be accepted. Share the photo as JPG, or set your iPhone camera to “Most Compatible” so new photos save as JPG.
Uploads fail on my phone but work on my computer. Why?
Usually an out-of-date app, a missing Photos or Files permission, or a file that’s only in cloud storage and not downloaded. Update the app, allow access and download the file first.
More help
Still failing?
Contact official Perplexity support
Include the file type and size, your device and app version, and the exact message. Don’t send private documents unless asked.