diff --git a/lnbits/app.py b/lnbits/app.py
index 4d7b0ca8b1..67d2e181f0 100644
--- a/lnbits/app.py
+++ b/lnbits/app.py
@@ -226,7 +226,6 @@ async def check_installed_extensions(app: FastAPI):
     persist state. Zips that are missing will be re-downloaded.
     """
 
-    shutil.rmtree(Path(settings.lnbits_extensions_path, "upgrades"), True)
     installed_extensions = await build_all_installed_extensions_list(False)
 
     for ext in installed_extensions:
@@ -336,8 +335,14 @@ def register_custom_extensions_path():
             + f" '{settings.lnbits_extensions_path}/extensions'"
         )
 
-    sys.path.append(str(Path(settings.lnbits_extensions_path, "extensions")))
-    sys.path.append(str(Path(settings.lnbits_extensions_path, "upgrades")))
+    extensions_dir = Path(settings.lnbits_extensions_path, "extensions")
+    Path(extensions_dir).mkdir(parents=True, exist_ok=True)
+    sys.path.append(str(extensions_dir))
+
+    upgrades_dir = Path(settings.lnbits_extensions_path, "upgrades")
+    shutil.rmtree(upgrades_dir, True)
+    Path(upgrades_dir).mkdir(parents=True, exist_ok=True)
+    sys.path.append(str(upgrades_dir))
 
 
 def register_new_ext_routes(app: FastAPI) -> Callable:
diff --git a/lnbits/core/models/extensions.py b/lnbits/core/models/extensions.py
index 3743e37c31..bf43ce54e4 100644
--- a/lnbits/core/models/extensions.py
+++ b/lnbits/core/models/extensions.py
@@ -169,7 +169,11 @@ def from_installable_ext(cls, ext_info: InstallableExtension) -> Extension:
             name=ext_info.name,
             short_description=ext_info.short_description,
             tile=ext_info.icon,
-            upgrade_hash=settings.extension_upgrade_hash(ext_info.id),
+            upgrade_hash=(
+                ext_info.hash
+                if settings.extension_has_been_activated(ext_info.id)
+                else ""
+            ),
         )
 
 
diff --git a/lnbits/core/services/extensions.py b/lnbits/core/services/extensions.py
index 3d3f611a66..7e54d93b62 100644
--- a/lnbits/core/services/extensions.py
+++ b/lnbits/core/services/extensions.py
@@ -12,19 +12,23 @@
     get_installed_extension,
     update_installed_extension_state,
 )
-from lnbits.core.crud.extensions import get_installed_extensions
+from lnbits.core.crud.extensions import (
+    get_installed_extensions,
+    update_installed_extension,
+)
 from lnbits.core.helpers import migrate_extension_database
 from lnbits.settings import settings
 
-from ..models.extensions import Extension, InstallableExtension
+from ..models.extensions import Extension, ExtensionMeta, InstallableExtension
 
 
 async def install_extension(ext_info: InstallableExtension) -> Extension:
     ext_id = ext_info.id
     extension = Extension.from_installable_ext(ext_info)
     installed_ext = await get_installed_extension(ext_id)
-    if installed_ext:
-        ext_info.meta = installed_ext.meta
+    if installed_ext and installed_ext.meta:
+        ext_info.meta = ext_info.meta or ExtensionMeta()
+        ext_info.meta.payments = installed_ext.meta.payments
 
     await ext_info.download_archive()
 
@@ -37,6 +41,8 @@ async def install_extension(ext_info: InstallableExtension) -> Extension:
     # if it does exist, it will be activated later in the code
     if not installed_ext:
         await create_installed_extension(ext_info)
+    else:
+        await update_installed_extension(ext_info)
 
     if extension.is_upgrade_extension:
         # call stop while the old routes are still active
diff --git a/lnbits/settings.py b/lnbits/settings.py
index 4c9e8e8530..12fff57418 100644
--- a/lnbits/settings.py
+++ b/lnbits/settings.py
@@ -126,7 +126,11 @@ class InstalledExtensionsSettings(LNbitsSettings):
     lnbits_extensions_redirects: list[RedirectPath] = Field(default=[])
 
     # list of all extension ids
-    lnbits_all_extensions_ids: set[Any] = Field(default=[])
+    lnbits_all_extensions_ids: set[str] = Field(default=[])
+
+    # list of all extension ids that have been activated at least once
+    # only add to this set, do not remove
+    lnbits_activated_paths_extensions_ids: set[str] = Field(default=[])
 
     def find_extension_redirect(
         self, path: str, req_headers: list[tuple[bytes, bytes]]
@@ -160,11 +164,15 @@ def activate_extension_paths(
             self._activate_extension_redirects(ext_id, ext_redirects)
 
         self.lnbits_all_extensions_ids.add(ext_id)
+        self.lnbits_activated_paths_extensions_ids.add(ext_id)
 
     def deactivate_extension_paths(self, ext_id: str):
         self.lnbits_deactivated_extensions.add(ext_id)
         self._remove_extension_redirects(ext_id)
 
+    def extension_has_been_activated(self, ext_id: str) -> bool:
+        return ext_id in settings.lnbits_activated_paths_extensions_ids
+
     def extension_upgrade_hash(self, ext_id: str) -> str:
         return settings.lnbits_upgraded_extensions.get(ext_id, "")