diff --git a/src/web/app/desktop/tags/drive/browser.tag b/src/web/app/desktop/tags/drive/browser.tag
index 7eaa7ed6e..9f3c14f82 100644
--- a/src/web/app/desktop/tags/drive/browser.tag
+++ b/src/web/app/desktop/tags/drive/browser.tag
@@ -516,13 +516,23 @@
 		};
 
 		this.chooseFile = file => {
-			if (this.selectedFiles.some(f => f.id == file.id)) {
-				this.selectedFiles = this.selectedFiles.filter(f => f.id != file.id);
+			const isAlreadySelected = this.selectedFiles.some(f => f.id == file.id);
+			if (this.multiple) {
+				if (isAlreadySelected) {
+					this.selectedFiles = this.selectedFiles.filter(f => f.id != file.id);
+				} else {
+					this.selectedFiles.push(file);
+				}
+				this.update();
+				this.trigger('change-selection', this.selectedFiles);
 			} else {
-				this.selectedFiles.push(file);
+				if (isAlreadySelected) {
+					this.trigger('selected', file);
+				} else {
+					this.selectedFiles = [file];
+					this.trigger('change-selection', [file]);
+				}
 			}
-			this.update();
-			this.trigger('change-selection', this.selectedFiles);
 		};
 
 		this.newWindow = folderId => {
diff --git a/src/web/app/desktop/tags/drive/file.tag b/src/web/app/desktop/tags/drive/file.tag
index 47416db0b..519d04f6d 100644
--- a/src/web/app/desktop/tags/drive/file.tag
+++ b/src/web/app/desktop/tags/drive/file.tag
@@ -156,6 +156,7 @@
 
 		this.browser.on('change-selection', selections => {
 			this.isSelected = selections.some(f => f.id == this.file.id);
+			this.update();
 		});
 
 		this.onclick = () => {
diff --git a/src/web/app/desktop/tags/select-file-from-drive-window.tag b/src/web/app/desktop/tags/select-file-from-drive-window.tag
index ed1c1bce6..5dba76d1f 100644
--- a/src/web/app/desktop/tags/select-file-from-drive-window.tag
+++ b/src/web/app/desktop/tags/select-file-from-drive-window.tag
@@ -142,7 +142,7 @@
 
 		this.on('mount', () => {
 			this.refs.window.refs.browser.on('selected', file => {
-				this.files = file;
+				this.files = [file];
 				this.ok();
 			});
 
@@ -166,7 +166,7 @@
 		};
 
 		this.ok = () => {
-			this.trigger('selected', this.files);
+			this.trigger('selected', this.multiple ? this.files : this.files[0]);
 			this.refs.window.close();
 		};
 	</script>