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In Geary, while browsing the Inbox (or any mail category), I can select a message item and drag it to the Trash, or to one of my many Labels.

I can also select multiple items by using Shift or Ctrl keys, but I can't drag them around. When I attempt click & drag on multiple selected items, only one will get dragged, while the rest of highlighted items go back to their unselected state.

Is this a bug or am I doing something wrong?

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Keep Shift or Ctrl pressed while drag them worked for me.

In my opinion this sounds like a Bug.
You can file a Bug about Geary here: https://bugzilla.gnome.org/enter_bug.cgi?product=geary

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