Upload files to AI tools without surprises
Every major AI assistant handles file uploads a little differently. These guides cover the file-size limits, format quirks, and Markdown workarounds for the six tools people actually use, across the six document types they actually upload.
Pick a format, pick a tool
36 guides, grouped by the file type you are working with.
PDF uploads
Convert PDF →OpenAI · 512MB cap · 128k context
Anthropic · 30MB cap · 200k context
Google · 100MB cap · 1000k context
Google · 200MB cap · 500k context
Perplexity AI · 25MB cap · 128k context
Microsoft · 512MB cap · 128k context
Word uploads
Convert Word →OpenAI · 512MB cap · 128k context
Anthropic · 30MB cap · 200k context
Google · 100MB cap · 1000k context
Google · 200MB cap · 500k context
Perplexity AI · 25MB cap · 128k context
Microsoft · 512MB cap · 128k context
Excel uploads
Convert Excel →OpenAI · 512MB cap · 128k context
Anthropic · 30MB cap · 200k context
Google · 100MB cap · 1000k context
Google · 200MB cap · 500k context
Perplexity AI · 25MB cap · 128k context
Microsoft · 512MB cap · 128k context
PowerPoint uploads
Convert PowerPoint →OpenAI · 512MB cap · 128k context
Anthropic · 30MB cap · 200k context
Google · 100MB cap · 1000k context
Google · 200MB cap · 500k context
Perplexity AI · 25MB cap · 128k context
Microsoft · 512MB cap · 128k context
EPUB uploads
Convert EPUB →OpenAI · 512MB cap · 128k context
Anthropic · 30MB cap · 200k context
Google · 100MB cap · 1000k context
Google · 200MB cap · 500k context
Perplexity AI · 25MB cap · 128k context
Microsoft · 512MB cap · 128k context
HTML uploads
Convert HTML →OpenAI · 512MB cap · 128k context
Anthropic · 30MB cap · 200k context
Google · 100MB cap · 1000k context
Google · 200MB cap · 500k context
Perplexity AI · 25MB cap · 128k context
Microsoft · 512MB cap · 128k context
Longer-form guides
End-to-end workflows that go beyond a single upload.
Convert once, upload anywhere
Markdown is the portable source format. Pick a converter and move on.