diff --git a/lib/livebook/utils.ex b/lib/livebook/utils.ex
index 6e2738d1d..0376e9d8c 100644
--- a/lib/livebook/utils.ex
+++ b/lib/livebook/utils.ex
@@ -277,6 +277,27 @@ defmodule Livebook.Utils do
     |> URI.to_string()
   end
 
+  @doc """
+  Infers file name from the given URL.
+
+  ## Examples
+
+      iex> Livebook.Utils.url_basename("https://example.com/data.csv")
+      "data.csv"
+
+      iex> Livebook.Utils.url_basename("https://example.com")
+      ""
+
+  """
+  @spec url_basename(String.t()) :: String.t()
+  def url_basename(url) do
+    uri = URI.parse(url)
+
+    (uri.path || "/")
+    |> String.split("/")
+    |> List.last()
+  end
+
   @doc ~S"""
   Wraps the given line into lines that fit in `width` characters.
 
diff --git a/lib/livebook_web/live/session_live/add_file_entry_file_component.ex b/lib/livebook_web/live/session_live/add_file_entry_file_component.ex
index 2a0b591da..16a6db54c 100644
--- a/lib/livebook_web/live/session_live/add_file_entry_file_component.ex
+++ b/lib/livebook_web/live/session_live/add_file_entry_file_component.ex
@@ -79,7 +79,7 @@ defmodule LivebookWeb.SessionLive.AddFileEntryFileComponent do
         phx-target={@myself}
       >
         <div class="flex flex-col space-y-4">
-          <.text_field field={f[:name]} label="Name" autocomplete="off" phx-debounce="blur" />
+          <.text_field field={f[:name]} label="Name" autocomplete="off" phx-debounce="200" />
           <.radio_field
             field={f[:copy]}
             options={[
diff --git a/lib/livebook_web/live/session_live/add_file_entry_upload_component.ex b/lib/livebook_web/live/session_live/add_file_entry_upload_component.ex
index 2b5342e67..a34eccd75 100644
--- a/lib/livebook_web/live/session_live/add_file_entry_upload_component.ex
+++ b/lib/livebook_web/live/session_live/add_file_entry_upload_component.ex
@@ -59,7 +59,7 @@ defmodule LivebookWeb.SessionLive.AddFileEntryUploadComponent do
             label="Name"
             id="add-file-entry-form-name"
             autocomplete="off"
-            phx-debounce="blur"
+            phx-debounce="200"
           />
         </div>
         <div class="mt-6 flex space-x-3">
diff --git a/lib/livebook_web/live/session_live/add_file_entry_url_component.ex b/lib/livebook_web/live/session_live/add_file_entry_url_component.ex
index f0677af5e..a954b6856 100644
--- a/lib/livebook_web/live/session_live/add_file_entry_url_component.ex
+++ b/lib/livebook_web/live/session_live/add_file_entry_url_component.ex
@@ -52,8 +52,21 @@ defmodule LivebookWeb.SessionLive.AddFileEntryUrlComponent do
         phx-target={@myself}
       >
         <div class="flex flex-col space-y-4">
-          <.text_field field={f[:url]} label="URL" autocomplete="off" phx-debounce="blur" />
-          <.text_field field={f[:name]} label="Name" autocomplete="off" phx-debounce="blur" />
+          <.text_field
+            field={f[:url]}
+            label="URL"
+            autocomplete="off"
+            phx-debounce="200"
+            phx-blur="url_blur"
+            phx-target={@myself}
+          />
+          <.text_field
+            field={f[:name]}
+            label="Name"
+            id="add-file-entry-form-name"
+            autocomplete="off"
+            phx-debounce="200"
+          />
           <.radio_field
             field={f[:copy]}
             options={[
@@ -86,6 +99,28 @@ defmodule LivebookWeb.SessionLive.AddFileEntryUrlComponent do
     {:noreply, assign(socket, changeset: changeset)}
   end
 
+  def handle_event("url_blur", %{"value" => url}, socket) do
+    name = Livebook.Utils.url_basename(url)
+
+    socket =
+      if socket.assigns.changeset.params["name"] == "" and name != "" do
+        # Emulate input event to make sure validation errors are shown
+        exec_js(
+          socket,
+          JS.dispatch("lb:set_value",
+            to: "#add-file-entry-form-name",
+            detail: %{value: name}
+          )
+          |> JS.dispatch("input", to: "#add-file-entry-form-name")
+          |> JS.dispatch("blur", to: "#add-file-entry-form-name")
+        )
+      else
+        socket
+      end
+
+    {:noreply, socket}
+  end
+
   def handle_event("add", %{"data" => data}, socket) do
     data
     |> changeset()
diff --git a/lib/livebook_web/live/session_live/files_list_component.ex b/lib/livebook_web/live/session_live/files_list_component.ex
index 37fda2996..dd7cb855d 100644
--- a/lib/livebook_web/live/session_live/files_list_component.ex
+++ b/lib/livebook_web/live/session_live/files_list_component.ex
@@ -110,7 +110,7 @@ defmodule LivebookWeb.SessionLive.FilesListComponent do
               <.menu_item>
                 <a
                   role="menuitem"
-                  href={~p"/sessions/#{@session.id}/files/download/#{file_entry.name}"}
+                  href={~p"/sessions/#{@session.id}/download/files/#{file_entry.name}"}
                 >
                   <.remix_icon icon="download-2-line" />
                   <span>Download</span>
diff --git a/lib/livebook_web/live/session_live/insert_image_component.ex b/lib/livebook_web/live/session_live/insert_image_component.ex
index 90b1ea807..e7e6f4847 100644
--- a/lib/livebook_web/live/session_live/insert_image_component.ex
+++ b/lib/livebook_web/live/session_live/insert_image_component.ex
@@ -64,7 +64,7 @@ defmodule LivebookWeb.SessionLive.InsertImageComponent do
             label="Name"
             id="insert-image-form-name"
             autocomplete="off"
-            phx-debounce="blur"
+            phx-debounce="200"
           />
         </div>
         <div class="mt-8 flex justify-end space-x-2">