diff --git a/internal/api/room/handler.go b/internal/api/room/handler.go
index 3d7026f7..247d3a14 100644
--- a/internal/api/room/handler.go
+++ b/internal/api/room/handler.go
@@ -69,6 +69,7 @@ func (h *RoomHandler) Route(r chi.Router) {
 
 	r.With(h.uploadMiddleware).Route("/upload", func(r chi.Router) {
 		r.Post("/drop", h.uploadDrop)
+		r.Post("/dialog", h.uploadDialog)
 	})
 }
 
diff --git a/internal/api/room/upload.go b/internal/api/room/upload.go
index e98d5ff3..cec1d8e3 100644
--- a/internal/api/room/upload.go
+++ b/internal/api/room/upload.go
@@ -86,3 +86,65 @@ func (h *RoomHandler) uploadDrop(w http.ResponseWriter, r *http.Request) {
 
 	utils.HttpSuccess(w)
 }
+
+
+func (h *RoomHandler) uploadDialog(w http.ResponseWriter, r *http.Request) {
+	r.ParseMultipartForm(MAX_UPLOAD_SIZE)
+
+	if r.MultipartForm == nil {
+		utils.HttpBadRequest(w, "No MultipartForm received.")
+		return
+	}
+
+	defer r.MultipartForm.RemoveAll()
+
+	if !h.desktop.IsFileChooserDialogOpen() {
+		utils.HttpBadRequest(w, "Open file chooser dialog first.")
+		return
+	}
+
+	req_files := r.MultipartForm.File["files"]
+	if len(req_files) == 0 {
+		utils.HttpBadRequest(w, "No files received.")
+		return
+	}
+
+	dir, err := ioutil.TempDir("", "neko-dialog-*")
+	if err != nil {
+		utils.HttpInternalServerError(w, err)
+		return
+	}
+
+	for _, req_file := range req_files {
+		path := path.Join(dir, req_file.Filename)
+
+		srcFile, err := req_file.Open()
+		if err != nil {
+			utils.HttpInternalServerError(w, err)
+			return
+		}
+
+		defer srcFile.Close()
+
+		dstFile, err := os.OpenFile(path, os.O_APPEND | os.O_CREATE | os.O_WRONLY, 0644)
+		if err != nil {
+			utils.HttpInternalServerError(w, err)
+			return
+		}
+
+		defer dstFile.Close()
+
+		_, err = io.Copy(dstFile, srcFile)
+		if err != nil {
+			utils.HttpInternalServerError(w, err)
+			return
+		}
+	}
+
+	if err := h.desktop.HandleFileChooserDialog(dir); err != nil {
+		utils.HttpInternalServerError(w, "Unable to handle file chooser dialog.")
+		return
+	}
+
+	utils.HttpSuccess(w)
+}
diff --git a/internal/desktop/filechooser.go b/internal/desktop/filechooser.go
new file mode 100644
index 00000000..9fc25af8
--- /dev/null
+++ b/internal/desktop/filechooser.go
@@ -0,0 +1,58 @@
+package desktop
+
+import (
+	"os/exec"
+)
+
+func (manager *DesktopManagerCtx) HandleFileChooserDialog(uri string) error {
+	mu.Lock()
+	defer mu.Unlock()
+
+	// TOOD: Use native API.
+    cmd := exec.Command(
+		"xdotool",
+			"search", "--name", "Open", "windowfocus",
+			"sleep", "0.2",
+			"key", "--clearmodifiers", "ctrl+l",
+			"type", "--args", "1", uri + "//",
+			"key", "--clearmodifiers", "Return",
+			"sleep", "1",
+			"key", "--clearmodifiers", "Down",
+			"key", "--clearmodifiers", "ctrl+a",
+			"key", "--clearmodifiers", "Return",
+			"sleep", "0.3",
+	)
+
+	_, err := cmd.Output()
+	return err
+}
+
+func (manager *DesktopManagerCtx) CloseFileChooserDialog() error {
+	mu.Lock()
+	defer mu.Unlock()
+
+	// TOOD: Use native API.
+    cmd := exec.Command(
+		"xdotool",
+			"search", "--name", "Open", "windowfocus",
+			"sleep", "0.2",
+			"key", "--clearmodifiers", "alt+f4",
+	)
+
+	_, err := cmd.Output()
+	return err
+}
+
+func (manager *DesktopManagerCtx) IsFileChooserDialogOpen() bool {
+	mu.Lock()
+	defer mu.Unlock()
+
+	// TOOD: Use native API.
+    cmd := exec.Command(
+		"xdotool",
+			"search", "--name", "Open", "windowfocus",
+	)
+
+	_, err := cmd.Output()
+	return err == nil
+}
diff --git a/internal/types/desktop.go b/internal/types/desktop.go
index a0aaad3b..7fa60538 100644
--- a/internal/types/desktop.go
+++ b/internal/types/desktop.go
@@ -66,4 +66,9 @@ type DesktopManager interface {
 
 	// drop
 	DropFiles(x int, y int, files []string) bool
+
+	// filechooser
+	HandleFileChooserDialog(uri string) error
+	CloseFileChooserDialog() error
+	IsFileChooserDialogOpen() bool
 }