diff --git a/frappe/core/doctype/file/file.py b/frappe/core/doctype/file/file.py
index 449fc572f4..13435d5d47 100755
--- a/frappe/core/doctype/file/file.py
+++ b/frappe/core/doctype/file/file.py
@@ -91,6 +91,7 @@ class File(Document):
 
 	def before_insert(self):
 		self.set_folder_name()
+		self.set_is_private()
 		self.set_file_name()
 		self.validate_attachment_limit()
 		self.set_file_type()
@@ -106,12 +107,11 @@ class File(Document):
 			self.flags.new_file = True
 			frappe.db.after_rollback.add(self.on_rollback)
 
+		self.validate_duplicate_entry()  # Hash is generated in save_file
+
 	def after_insert(self):
 		if not self.is_folder:
 			self.create_attachment_record()
-		self.set_is_private()
-		self.set_file_name()
-		self.validate_duplicate_entry()
 
 	def validate(self):
 		if self.is_folder:
@@ -470,7 +470,12 @@ class File(Document):
 		"""If file not attached to any other record, delete it"""
 		on_disk_file_not_shared = self.content_hash and not frappe.get_all(
 			"File",
-			filters={"content_hash": self.content_hash, "name": ["!=", self.name]},
+			filters={
+				"content_hash": self.content_hash,
+				"name": ["!=", self.name],
+				# NOTE: Some old Files might share file_urls while not sharing the is_private value
+				# "is_private": self.is_private,
+			},
 			limit=1,
 		)
 		if on_disk_file_not_shared:
diff --git a/frappe/core/doctype/file/test_file.py b/frappe/core/doctype/file/test_file.py
index 03a8927dac..57159fa48d 100644
--- a/frappe/core/doctype/file/test_file.py
+++ b/frappe/core/doctype/file/test_file.py
@@ -920,3 +920,41 @@ class TestGuestFileAndAttachments(FrappeTestCase):
 		).insert(ignore_permissions=True)
 
 		self.assertFalse(file.is_downloadable())
+
+	def test_private_remains_private_even_if_same_hash(self):
+		file_name = "test" + frappe.generate_hash()
+		content = file_name.encode()
+
+		doc_pub: "File" = frappe.new_doc("File")  # type: ignore
+		doc_pub.file_url = f"/files/{file_name}.txt"
+		doc_pub.content = content
+		doc_pub.save()
+
+		doc_pri: "File" = frappe.new_doc("File")  # type: ignore
+		doc_pri.file_url = f"/private/files/{file_name}.txt"
+		doc_pri.is_private = False
+		doc_pri.content = content
+		doc_pri.save()
+
+		doc_pub.reload()
+		doc_pri.reload()
+
+		self.assertEqual(doc_pub.is_private, 0)
+		self.assertEqual(doc_pri.is_private, 1)
+
+		self.assertEqual(doc_pub.file_url, f"/files/{file_name}.txt")
+		self.assertEqual(doc_pri.file_url, f"/private/files/{file_name}.txt")
+
+		self.assertEqual(doc_pub.get_content(), content)
+		self.assertEqual(doc_pri.get_content(), content)
+
+		# Deleting a public File should not delete the private File's disk file
+		doc_pub.delete()
+		self.assertTrue(os.path.exists(doc_pri.get_full_path()))
+
+		# TODO: Migrate existing Files that have a mismatch between `is_private` and `file_url` prefix?
+		# self.assertFalse(os.path.exists(doc_pub.get_full_path()))
+
+		self.assertEqual(doc_pri.get_content(), content)
+		doc_pri.delete()
+		self.assertFalse(os.path.exists(doc_pri.get_full_path()))