diff --git a/shiny/_app.py b/shiny/_app.py
index 0de886a69..835e93a10 100644
--- a/shiny/_app.py
+++ b/shiny/_app.py
@@ -2,6 +2,8 @@
 
 import copy
 import os
+import shutil
+import tempfile
 import secrets
 from contextlib import AsyncExitStack, asynccontextmanager
 from inspect import signature
@@ -214,6 +216,25 @@ def __init__(
                 cast("Tag | TagList", ui), lib_prefix=self.lib_prefix
             )
 
+    def __del__(self):
+        current_temp_dir = os.path.realpath(tempfile.gettempdir())
+
+        user_dependencies = [
+            v.source["subdir"]
+            for k, v in self._registered_dependencies.items()
+            if k.startswith("include-")
+        ]
+
+        for item in user_dependencies:
+            # Only remove the item if it exists and it is in the current temp directory
+            if (
+                os.path.exists(item)
+                and os.path.commonprefix([os.path.realpath(item), current_temp_dir])
+                == current_temp_dir
+            ):
+                print("Removing dependency: ", item)
+                shutil.rmtree(item)
+
     def init_starlette_app(self) -> starlette.applications.Starlette:
         routes: list[starlette.routing.BaseRoute] = [
             starlette.routing.WebSocketRoute("/websocket/", self._on_connect_cb),
diff --git a/shiny/ui/_include_helpers.py b/shiny/ui/_include_helpers.py
index 3c0c9409a..3c7fa923e 100644
--- a/shiny/ui/_include_helpers.py
+++ b/shiny/ui/_include_helpers.py
@@ -214,25 +214,42 @@ def create_include_dependency(
 
 def maybe_copy_files(path: Path | str, include_files: bool) -> tuple[str, str]:
     hash = get_hash(path, include_files)
+    print("path: ", path, "Hash: ", hash)
 
-    # To avoid unnecessary work when the same file is included multiple times,
-    # use a directory scoped by a hash of the file.
-    tmpdir = os.path.join(tempfile.gettempdir(), "shiny_include_files", hash)
+    tmpdir = os.path.join(tempfile.gettempdir(), f"shiny_include_{hash}")
     path_dest = os.path.join(tmpdir, os.path.basename(path))
+    print("tmpdir: ", tmpdir, "path_dest: ", path_dest)
 
+    # To avoid unnecessary work when the same file is included multiple times,
+    # use a directory scoped by a hash of the file.
     # Since the hash/tmpdir should represent all the files in the path's directory,
-    # we can simply return here
+    # we can check if it exists to determine if we have a cache hit
     if os.path.exists(path_dest):
+        print("Path already exists:", path_dest)
         return path_dest, hash
 
     # Otherwise, make sure we have a clean slate
     if os.path.exists(tmpdir):
+        print("Folder already exists, but not files, removing.")
         shutil.rmtree(tmpdir)
 
     if include_files:
+        print(
+            "Copying all included files from: ",
+            path,
+            " with perms: ",
+            oct(os.stat(path).st_mode),
+        )
         shutil.copytree(os.path.dirname(path), tmpdir)
+
     else:
         os.makedirs(tmpdir, exist_ok=True)
+        print(
+            "Copying files from: ",
+            path,
+            " with perms: ",
+            oct(os.stat(path).st_mode),
+        )
         shutil.copy(path, path_dest)
 
     return path_dest, hash
@@ -240,11 +257,12 @@ def maybe_copy_files(path: Path | str, include_files: bool) -> tuple[str, str]:
 
 def get_hash(path: Path | str, include_files: bool) -> str:
     if include_files:
-        key = get_file_key(path)
-    else:
         dir = os.path.dirname(path)
         files = glob.iglob(os.path.join(dir, "**"), recursive=True)
         key = "\n".join([get_file_key(x) for x in files])
+    else:
+        key = get_file_key(path)
+
     return hash_deterministic(key)
 
 
diff --git a/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/app.py b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/app.py
new file mode 100644
index 000000000..c8e979769
--- /dev/null
+++ b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/app.py
@@ -0,0 +1,27 @@
+from pathlib import Path
+
+from shiny import App, Inputs, Outputs, Session, ui
+
+js_file = Path(__file__).parent / "js" / "customjs.js"
+css_file = Path(__file__).parent / "css" / "style.css"
+
+# Define the UI
+app_ui = ui.page_fluid(
+    ui.include_css(css_file, method="link_files"),
+    ui.include_js(js_file, method="link_files"),
+    ui.h1("Simple Shiny App with External CSS"),
+    ui.div(
+        ui.p("This is a simple Shiny app that demonstrates ui.include_css()"),
+        ui.p("The styling comes from an external CSS file!"),
+        class_="content",
+    ),
+)
+
+
+# Define the server
+def server(input: Inputs, output: Outputs, session: Session):
+    pass
+
+
+# Create and run the app
+app = App(app_ui, server)
diff --git a/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/css/evenmorecss/more.css b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/css/evenmorecss/more.css
new file mode 100644
index 000000000..3eda1891b
--- /dev/null
+++ b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/css/evenmorecss/more.css
@@ -0,0 +1,3 @@
+body {
+  background-color: #c8e1f7;
+}
\ No newline at end of file
diff --git a/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/css/style.css b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/css/style.css
new file mode 100644
index 000000000..99c3ee888
--- /dev/null
+++ b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/css/style.css
@@ -0,0 +1,21 @@
+@import url("./evenmorecss/more.css");
+
+body {
+  font-family: Arial, sans-serif;
+}
+
+h1 {
+  color: black;
+  border-bottom: 2px solid #4682b4;
+  padding-bottom: 10px;
+}
+
+.content {
+  margin: 20px;
+  padding: 15px;
+  background-color: white;
+  border-radius: 5px;
+  box-shadow: 0 0 10px rgba(0, 0, 0, 0.1);
+}
+
+
diff --git a/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/js/customjs.js b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/js/customjs.js
new file mode 100644
index 000000000..4dc8fcc69
--- /dev/null
+++ b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/js/customjs.js
@@ -0,0 +1,4 @@
+const newParagraph = document.createElement('p');
+newParagraph.textContent = 'Heyo!';
+document.body.appendChild(newParagraph);
+
diff --git a/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/test_css-js-inclusion.py b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/test_css-js-inclusion.py
new file mode 100644
index 000000000..b144f78f6
--- /dev/null
+++ b/tests/playwright/shiny/bugs/2061-css-js-inclusion/include_files_case/test_css-js-inclusion.py
@@ -0,0 +1,9 @@
+from playwright.sync_api import Page, expect
+
+from shiny.run import ShinyAppProc
+
+
+def test_inclusion(page: Page, local_app: ShinyAppProc) -> None:
+    page.goto(local_app.url)
+
+    expect(page.locator("body > p")).to_have_text("Heyo!")
diff --git a/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/app.py b/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/app.py
new file mode 100644
index 000000000..4072ca609
--- /dev/null
+++ b/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/app.py
@@ -0,0 +1,27 @@
+from pathlib import Path
+
+from shiny import App, Inputs, Outputs, Session, ui
+
+js_file = Path(__file__).parent / "customjs.js"
+css_file = Path(__file__).parent / "style.css"
+
+# Define the UI
+app_ui = ui.page_fluid(
+    ui.include_css(css_file, method="link"),
+    ui.include_js(js_file, method="link"),
+    ui.h1("Simple Shiny App with External CSS"),
+    ui.div(
+        ui.p("This is a simple Shiny app that demonstrates ui.include_css()"),
+        ui.p("The styling comes from an external CSS file!"),
+        class_="content",
+    ),
+)
+
+
+# Define the server
+def server(input: Inputs, output: Outputs, session: Session):
+    pass
+
+
+# Create and run the app
+app = App(app_ui, server)
diff --git a/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/customjs.js b/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/customjs.js
new file mode 100644
index 000000000..c7e8ae251
--- /dev/null
+++ b/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/customjs.js
@@ -0,0 +1,3 @@
+const newParagraph = document.createElement('p');
+newParagraph.textContent = 'Heyo!';
+document.body.appendChild(newParagraph);
diff --git a/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/style.css b/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/style.css
new file mode 100644
index 000000000..078238b67
--- /dev/null
+++ b/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/style.css
@@ -0,0 +1,18 @@
+body {
+  background-color: #70bfef;
+  font-family: Arial, sans-serif;
+}
+
+h1 {
+  color: black;
+  border-bottom: 2px solid #4682b4;
+  padding-bottom: 10px;
+}
+
+.content {
+  margin: 20px;
+  padding: 15px;
+  background-color: white;
+  border-radius: 5px;
+  box-shadow: 0 0 10px rgba(0, 0, 0, 0.1);
+}
diff --git a/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/test_css-js-inclusion.py b/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/test_css-js-inclusion.py
new file mode 100644
index 000000000..b144f78f6
--- /dev/null
+++ b/tests/playwright/shiny/bugs/2061-css-js-inclusion/not_include_files_case/test_css-js-inclusion.py
@@ -0,0 +1,9 @@
+from playwright.sync_api import Page, expect
+
+from shiny.run import ShinyAppProc
+
+
+def test_inclusion(page: Page, local_app: ShinyAppProc) -> None:
+    page.goto(local_app.url)
+
+    expect(page.locator("body > p")).to_have_text("Heyo!")