diff --git a/src/components/Editor/MediaHandler.vue b/src/components/Editor/MediaHandler.vue
index 1f04e62b465..c32bc8ec08b 100644
--- a/src/components/Editor/MediaHandler.vue
+++ b/src/components/Editor/MediaHandler.vue
@@ -194,7 +194,18 @@ export default {
 				? this.$editor.chain().focus(position)
 				: this.$editor.chain()
 
-			chain.setImage({ src, alt }).insertContent('<br />').focus().run()
+			chain.setImage({ src, alt }).run()
+
+			const selection = this.$editor.view.state.selection
+			if (selection.from === 0 && !selection.empty) {
+				// If inserted image is first element, it is selected and would get overwritten by
+				// subsequent editor inserts (see tiptap#3355). So unselect the image by placing
+				// the cursor at the end of the selection.
+				this.$editor.commands.focus(selection.to)
+			}
+
+			// Insert a newline to allow placing the cursor in between subsequent images
+			this.$editor.chain().insertContent('<br />').focus().run()
 		},
 	},
 }