Dropper

Dropper is a macOS menu bar application that handles file sharing through Cloudflare R2, the S3 compatible object storage service with zero egress fees. The workflow is simple: drag any file onto the menu bar icon, wait a moment for upload, and the shareable link lands in your clipboard ready to paste. Files go directly to your own R2 bucket rather than through any intermediary storage that Dropper controls. This means the app never sees your data, links work even if Dropper disappears as a company, and your storage costs scale with Cloudflare's pricing rather than some monthly subscription that might increase over time or limit your usage arbitrarily.

What makes Dropper more than a basic upload tool is the automatic format conversion that happens before files hit the bucket. HEIC images convert to JPEG so recipients on Windows or Android can view them without special software or hunting for codec downloads. AIFF audio converts to WAV for cross-platform compatibility. MOV and HEVC video files convert to MP4 with H.264, though videos already in H.264 get remuxed rather than re-encoded to preserve quality and complete faster. These conversions happen losslessly where possible, and they solve the constant friction of sending files to people whose devices don't support Apple's preferred formats. You don't have to think about what format the recipient can handle because Dropper normalizes everything automatically.

The share pages themselves are designed thoughtfully rather than being generic file download screens with a button and nothing else. Images display in a dark focused viewer with optional gallery mode and lightbox navigation for collections. Audio files get a SoundCloud style player with computed waveforms showing the track structure. Video plays in a custom player with scrubbing controls that work smoothly even on longer files. Markdown and text files render with proper formatting so documentation or notes display readably without downloading. PDFs embed natively in the browser for immediate viewing. Anything the app doesn't recognize shows as a clean download card with file type and size information. All of this serves from your own bucket so the pages load fast and don't depend on Dropper's servers staying online or performing well.

Collections let you share multiple files through a single link rather than sending several URLs separately. Drag several files at once or add more to an existing collection later after it's already been shared. Items can be reordered by dragging within the collection view, and the resulting page displays everything together in a coherent layout. For designers sending mockup variations to clients or musicians sharing stems with collaborators, this beats the clunky folder download experience that most file sharing services offer where recipients have to download a zip and extract it locally. Each share gets a human readable name combined with an unguessable random suffix, balancing discoverability for you with security against random access. Links don't require accounts or passwords to access, which removes friction for recipients who just want to see what you sent without creating yet another account somewhere.

Organization features keep the link history manageable over time as you accumulate hundreds of shares. Shares can be archived without breaking links, so old uploads stay accessible but don't clutter your dropdown with outdated files from months ago. Important evergreen links pin to the top of the list for quick access when you share the same resources repeatedly. Folder browsing with breadcrumbs helps navigate if you upload entire directory structures for larger projects. For anything involving sensitive files, the unlisted by default approach means links only work for people who have the URL. There's no public gallery, search indexing, or exposure to anyone who doesn't receive the link directly from you.

Built in screenshot annotation lets you capture and mark up screen content before sharing it. This saves the round trip of taking a screenshot, opening it in Preview or another app, adding annotations, saving, and then uploading separately. For designers giving feedback, developers reporting bugs, or anyone who regularly shares annotated screenshots, having this integrated directly into the sharing workflow cuts several steps out of the process.

Setup takes about three minutes through a guided wizard that connects your Cloudflare account, enables your bucket's public r2.dev URL, and stores the API token securely in macOS Keychain rather than in a config file that could be exposed. Custom domains can attach to buckets if you want branded share URLs that use your own domain rather than Cloudflare's default subdomain. Cloudflare's free tier includes 10 GB of storage with zero egress fees, meaning you pay nothing until you exceed that threshold and then only for what you actually store since downloads don't cost extra. The app itself is free with no subscription or premium tier. Source code lives on GitHub under a source available license, so the codebase can be inspected even if the license isn't strictly permissive open source. Requirements are macOS 14 or later running on either Apple silicon or Intel Macs.