The five ways to upload
Dropline has five entry points, and every one of them is somewhere macOS already put your hands. However a file gets in, it leaves the same way: the URL on your clipboard, plus a system notification.
1. The window
Open Dropline and drop files onto it. The window is the only place that shows the full queue — one row per file, each with its own progress bar, and the history list underneath.
Drop a folder and Dropline expands it, uploading the files inside.
2. The Dock icon
Drag a file onto the Dropline icon in the Dock without opening anything. The upload starts immediately; the window does not come forward.
If you never want a Dock icon, turn on Settings → General → Hide the Dock icon (menu bar only). Dropline then runs as a menu bar app with no Dock presence and no ⌘-Tab entry.
3. The Finder context menu
Right-click any file in Finder and choose Upload with Dropline. It sits at the top level of the menu, not buried under Services.
This comes from a Finder extension, which macOS keeps switched off until you approve it — see Install. Three display modes are available under Settings → General → Finder Context Menu:
| Mode | What you get |
|---|---|
| Show (with icon) | The item, with an upload glyph beside it |
| Show (without icon) | The item, plain, matching the system's own entries |
| Don't show | Nothing in the context menu; every other way still works |
The change takes effect immediately — no Finder restart.
As a Services shortcut
The same command appears under System Settings → Keyboard → Keyboard Shortcuts → Services → Files and Folders, where you can bind it to a key combination. Select files in Finder, press the key, done.
4. The clipboard
Copy an image and upload it without ever writing it to disk. This is the fast
path for screenshots: press ⇧⌘4, drag a region, then upload from the clipboard
— macOS puts the screenshot on the clipboard when you hold ⌃ while capturing,
or you can use the on-screen capture bar's clipboard option.
Clipboard uploads are also how you move an image out of a browser, a chat window or Preview without saving a file first.
5. The menu bar
The menu bar icon is the app's real home.
- Upload… opens the system file panel.
- The last five links sit in the menu, one click from being copied again.
- The icon turns into a progress ring while an upload runs, showing overall progress without you switching to anything.
What happens on finish
The same three things happen for all five, and each is a switch in Settings → General:
- The link goes on your clipboard — as a bare URL, or as
with Copy as Markdown on. - A system notification fires, naming the file.
- The record joins the history, which keeps the last 300 uploads and surfaces the last five in the menu bar.
Large files and concurrency
Any file type is accepted. Large ones — video especially — are streamed from a temporary file rather than held in memory, so a two-gigabyte upload costs the same RAM as a screenshot.
Uploads run concurrently, three at a time by default, adjustable to 1, 2, 3, 5 or 8 under Settings → General → Concurrent uploads. The transfer timeout is one hour per file, so slow links and big videos do not get cut off.