diff --git a/src/duckdb/extension/parquet/parquet_writer.cpp b/src/duckdb/extension/parquet/parquet_writer.cpp
index 01ef727a2..3c6d11d9a 100644
--- a/src/duckdb/extension/parquet/parquet_writer.cpp
+++ b/src/duckdb/extension/parquet/parquet_writer.cpp
@@ -12,6 +12,7 @@
 #include "duckdb/common/serializer/write_stream.hpp"
 #include "duckdb/common/string_util.hpp"
 #include "duckdb/function/table_function.hpp"
+#include "duckdb/main/extension_helper.hpp"
 #include "duckdb/main/client_context.hpp"
 #include "duckdb/main/connection.hpp"
 #include "duckdb/parser/parsed_data/create_copy_function_info.hpp"
@@ -374,6 +375,12 @@ ParquetWriter::ParquetWriter(ClientContext &context, FileSystem &fs, string file
 
 	if (encryption_config) {
 		auto &config = DBConfig::GetConfig(context);
+
+		// To ensure we can write, we need to autoload httpfs
+		if (!config.encryption_util || !config.encryption_util->SupportsEncryption()) {
+			ExtensionHelper::TryAutoLoadExtension(context, "httpfs");
+		}
+
 		if (config.encryption_util && debug_use_openssl) {
 			// Use OpenSSL
 			encryption_util = config.encryption_util;
diff --git a/src/duckdb/src/common/encryption_key_manager.cpp b/src/duckdb/src/common/encryption_key_manager.cpp
index 482c4a006..2e75a7e8b 100644
--- a/src/duckdb/src/common/encryption_key_manager.cpp
+++ b/src/duckdb/src/common/encryption_key_manager.cpp
@@ -19,7 +19,8 @@ EncryptionKey::EncryptionKey(data_ptr_t encryption_key_p) {
 	D_ASSERT(memcmp(key, encryption_key_p, MainHeader::DEFAULT_ENCRYPTION_KEY_LENGTH) == 0);
 
 	// zero out the encryption key in memory
-	memset(encryption_key_p, 0, MainHeader::DEFAULT_ENCRYPTION_KEY_LENGTH);
+	duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLS::SecureClearData(encryption_key_p,
+	                                                                 MainHeader::DEFAULT_ENCRYPTION_KEY_LENGTH);
 	LockEncryptionKey(key);
 }
 
@@ -37,7 +38,7 @@ void EncryptionKey::LockEncryptionKey(data_ptr_t key, idx_t key_len) {
 }
 
 void EncryptionKey::UnlockEncryptionKey(data_ptr_t key, idx_t key_len) {
-	memset(key, 0, key_len);
+	duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLS::SecureClearData(key, key_len);
 #if defined(_WIN32)
 	VirtualUnlock(key, key_len);
 #else
@@ -64,7 +65,8 @@ EncryptionKeyManager &EncryptionKeyManager::Get(DatabaseInstance &db) {
 
 string EncryptionKeyManager::GenerateRandomKeyID() {
 	uint8_t key_id[KEY_ID_BYTES];
-	duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLS::GenerateRandomDataStatic(key_id, KEY_ID_BYTES);
+	RandomEngine engine;
+	engine.RandomData(key_id, KEY_ID_BYTES);
 	string key_id_str(reinterpret_cast<const char *>(key_id), KEY_ID_BYTES);
 	return key_id_str;
 }
@@ -72,7 +74,7 @@ string EncryptionKeyManager::GenerateRandomKeyID() {
 void EncryptionKeyManager::AddKey(const string &key_name, data_ptr_t key) {
 	derived_keys.emplace(key_name, EncryptionKey(key));
 	// Zero-out the encryption key
-	std::memset(key, 0, DERIVED_KEY_LENGTH);
+	duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLS::SecureClearData(key, DERIVED_KEY_LENGTH);
 }
 
 bool EncryptionKeyManager::HasKey(const string &key_name) const {
@@ -107,7 +109,7 @@ string EncryptionKeyManager::Base64Decode(const string &key) {
 	auto output = duckdb::unique_ptr<unsigned char[]>(new unsigned char[result_size]);
 	Blob::FromBase64(key, output.get(), result_size);
 	string decoded_key(reinterpret_cast<const char *>(output.get()), result_size);
-	memset(output.get(), 0, result_size);
+	duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLS::SecureClearData(output.get(), result_size);
 	return decoded_key;
 }
 
@@ -124,10 +126,9 @@ void EncryptionKeyManager::DeriveKey(string &user_key, data_ptr_t salt, data_ptr
 
 	KeyDerivationFunctionSHA256(reinterpret_cast<const_data_ptr_t>(decoded_key.data()), decoded_key.size(), salt,
 	                            derived_key);
-
-	// wipe the original and decoded key
-	std::fill(user_key.begin(), user_key.end(), 0);
-	std::fill(decoded_key.begin(), decoded_key.end(), 0);
+	duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLS::SecureClearData(data_ptr_cast(&user_key[0]), user_key.size());
+	duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLS::SecureClearData(data_ptr_cast(&decoded_key[0]),
+	                                                                 decoded_key.size());
 	user_key.clear();
 	decoded_key.clear();
 }
diff --git a/src/duckdb/src/common/random_engine.cpp b/src/duckdb/src/common/random_engine.cpp
index 78403e030..156b4baec 100644
--- a/src/duckdb/src/common/random_engine.cpp
+++ b/src/duckdb/src/common/random_engine.cpp
@@ -82,4 +82,14 @@ void RandomEngine::SetSeed(uint64_t seed) {
 	random_state->pcg.seed(seed);
 }
 
+void RandomEngine::RandomData(duckdb::data_ptr_t data, duckdb::idx_t len) {
+	while (len) {
+		const auto random_integer = NextRandomInteger();
+		const auto next = duckdb::MinValue<duckdb::idx_t>(len, sizeof(random_integer));
+		memcpy(data, duckdb::const_data_ptr_cast(&random_integer), next);
+		data += next;
+		len -= next;
+	}
+}
+
 } // namespace duckdb
diff --git a/src/duckdb/src/execution/operator/scan/physical_table_scan.cpp b/src/duckdb/src/execution/operator/scan/physical_table_scan.cpp
index e9f66bea4..a777689b1 100644
--- a/src/duckdb/src/execution/operator/scan/physical_table_scan.cpp
+++ b/src/duckdb/src/execution/operator/scan/physical_table_scan.cpp
@@ -259,7 +259,7 @@ bool PhysicalTableScan::Equals(const PhysicalOperator &other_p) const {
 		return false;
 	}
 	auto &other = other_p.Cast<PhysicalTableScan>();
-	if (function.function != other.function.function) {
+	if (function != other.function) {
 		return false;
 	}
 	if (column_ids != other.column_ids) {
diff --git a/src/duckdb/src/function/table/version/pragma_version.cpp b/src/duckdb/src/function/table/version/pragma_version.cpp
index 1a5fb1fc6..7f9e18bc6 100644
--- a/src/duckdb/src/function/table/version/pragma_version.cpp
+++ b/src/duckdb/src/function/table/version/pragma_version.cpp
@@ -1,5 +1,5 @@
 #ifndef DUCKDB_PATCH_VERSION
-#define DUCKDB_PATCH_VERSION "2-dev305"
+#define DUCKDB_PATCH_VERSION "2-dev332"
 #endif
 #ifndef DUCKDB_MINOR_VERSION
 #define DUCKDB_MINOR_VERSION 4
@@ -8,10 +8,10 @@
 #define DUCKDB_MAJOR_VERSION 1
 #endif
 #ifndef DUCKDB_VERSION
-#define DUCKDB_VERSION "v1.4.2-dev305"
+#define DUCKDB_VERSION "v1.4.2-dev332"
 #endif
 #ifndef DUCKDB_SOURCE_ID
-#define DUCKDB_SOURCE_ID "8090b8d52e"
+#define DUCKDB_SOURCE_ID "0efe5ccb5b"
 #endif
 #include "duckdb/function/table/system_functions.hpp"
 #include "duckdb/main/database.hpp"
diff --git a/src/duckdb/src/function/table_function.cpp b/src/duckdb/src/function/table_function.cpp
index 310f75b58..a87a2d234 100644
--- a/src/duckdb/src/function/table_function.cpp
+++ b/src/duckdb/src/function/table_function.cpp
@@ -37,6 +37,30 @@ TableFunction::TableFunction(const vector<LogicalType> &arguments, table_functio
 TableFunction::TableFunction() : TableFunction("", {}, nullptr, nullptr, nullptr, nullptr) {
 }
 
+bool TableFunction::operator==(const TableFunction &rhs) const {
+	return name == rhs.name && arguments == rhs.arguments && varargs == rhs.varargs && bind == rhs.bind &&
+	       bind_replace == rhs.bind_replace && bind_operator == rhs.bind_operator && init_global == rhs.init_global &&
+	       init_local == rhs.init_local && function == rhs.function && in_out_function == rhs.in_out_function &&
+	       in_out_function_final == rhs.in_out_function_final && statistics == rhs.statistics &&
+	       dependency == rhs.dependency && cardinality == rhs.cardinality &&
+	       pushdown_complex_filter == rhs.pushdown_complex_filter && pushdown_expression == rhs.pushdown_expression &&
+	       to_string == rhs.to_string && dynamic_to_string == rhs.dynamic_to_string &&
+	       table_scan_progress == rhs.table_scan_progress && get_partition_data == rhs.get_partition_data &&
+	       get_bind_info == rhs.get_bind_info && type_pushdown == rhs.type_pushdown &&
+	       get_multi_file_reader == rhs.get_multi_file_reader && supports_pushdown_type == rhs.supports_pushdown_type &&
+	       get_partition_info == rhs.get_partition_info && get_partition_stats == rhs.get_partition_stats &&
+	       get_virtual_columns == rhs.get_virtual_columns && get_row_id_columns == rhs.get_row_id_columns &&
+	       serialize == rhs.serialize && deserialize == rhs.deserialize &&
+	       verify_serialization == rhs.verify_serialization && projection_pushdown == rhs.projection_pushdown &&
+	       filter_pushdown == rhs.filter_pushdown && filter_prune == rhs.filter_prune &&
+	       sampling_pushdown == rhs.sampling_pushdown && late_materialization == rhs.late_materialization &&
+	       global_initialization == rhs.global_initialization;
+}
+
+bool TableFunction::operator!=(const TableFunction &rhs) const {
+	return !(*this == rhs);
+}
+
 bool TableFunction::Equal(const TableFunction &rhs) const {
 	// number of types
 	if (this->arguments.size() != rhs.arguments.size()) {
diff --git a/src/duckdb/src/include/duckdb/common/encryption_key_manager.hpp b/src/duckdb/src/include/duckdb/common/encryption_key_manager.hpp
index 55c3aed75..446b64758 100644
--- a/src/duckdb/src/include/duckdb/common/encryption_key_manager.hpp
+++ b/src/duckdb/src/include/duckdb/common/encryption_key_manager.hpp
@@ -66,6 +66,8 @@ class EncryptionKeyManager : public ObjectCacheEntry {
 	static void KeyDerivationFunctionSHA256(data_ptr_t user_key, idx_t user_key_size, data_ptr_t salt,
 	                                        data_ptr_t derived_key);
 	static string Base64Decode(const string &key);
+
+	//! Generate a (non-cryptographically secure) random key ID
 	static string GenerateRandomKeyID();
 
 public:
diff --git a/src/duckdb/src/include/duckdb/common/encryption_state.hpp b/src/duckdb/src/include/duckdb/common/encryption_state.hpp
index 32c0597a9..845a45a9d 100644
--- a/src/duckdb/src/include/duckdb/common/encryption_state.hpp
+++ b/src/duckdb/src/include/duckdb/common/encryption_state.hpp
@@ -59,6 +59,11 @@ class EncryptionUtil {
 
 	virtual ~EncryptionUtil() {
 	}
+
+	//! Whether the EncryptionUtil supports encryption (some may only support decryption)
+	DUCKDB_API virtual bool SupportsEncryption() {
+		return true;
+	}
 };
 
 } // namespace duckdb
diff --git a/src/duckdb/src/include/duckdb/common/http_util.hpp b/src/duckdb/src/include/duckdb/common/http_util.hpp
index 125913348..11fc26c48 100644
--- a/src/duckdb/src/include/duckdb/common/http_util.hpp
+++ b/src/duckdb/src/include/duckdb/common/http_util.hpp
@@ -216,6 +216,7 @@ struct PostRequestInfo : public BaseRequest {
 class HTTPClient {
 public:
 	virtual ~HTTPClient() = default;
+	virtual void Initialize(HTTPParams &http_params) = 0;
 
 	virtual unique_ptr<HTTPResponse> Get(GetRequestInfo &info) = 0;
 	virtual unique_ptr<HTTPResponse> Put(PutRequestInfo &info) = 0;
diff --git a/src/duckdb/src/include/duckdb/common/random_engine.hpp b/src/duckdb/src/include/duckdb/common/random_engine.hpp
index 8a5a3097e..ec14b42e5 100644
--- a/src/duckdb/src/include/duckdb/common/random_engine.hpp
+++ b/src/duckdb/src/include/duckdb/common/random_engine.hpp
@@ -38,6 +38,8 @@ class RandomEngine {
 
 	void SetSeed(uint64_t seed);
 
+	void RandomData(duckdb::data_ptr_t data, duckdb::idx_t len);
+
 	static RandomEngine &Get(ClientContext &context);
 
 	mutex lock;
diff --git a/src/duckdb/src/include/duckdb/function/table_function.hpp b/src/duckdb/src/include/duckdb/function/table_function.hpp
index f6c9cc55e..6da688d04 100644
--- a/src/duckdb/src/include/duckdb/function/table_function.hpp
+++ b/src/duckdb/src/include/duckdb/function/table_function.hpp
@@ -432,6 +432,8 @@ class TableFunction : public SimpleNamedParameterFunction { // NOLINT: work-arou
 	TableFunctionInitialization global_initialization = TableFunctionInitialization::INITIALIZE_ON_EXECUTE;
 
 	DUCKDB_API bool Equal(const TableFunction &rhs) const;
+	DUCKDB_API bool operator==(const TableFunction &rhs) const;
+	DUCKDB_API bool operator!=(const TableFunction &rhs) const;
 };
 
 } // namespace duckdb
diff --git a/src/duckdb/src/include/duckdb/main/database.hpp b/src/duckdb/src/include/duckdb/main/database.hpp
index 860912130..7e43de600 100644
--- a/src/duckdb/src/include/duckdb/main/database.hpp
+++ b/src/duckdb/src/include/duckdb/main/database.hpp
@@ -69,7 +69,7 @@ class DatabaseInstance : public enable_shared_from_this<DatabaseInstance> {
 
 	DUCKDB_API SettingLookupResult TryGetCurrentSetting(const string &key, Value &result) const;
 
-	DUCKDB_API shared_ptr<EncryptionUtil> GetEncryptionUtil() const;
+	DUCKDB_API shared_ptr<EncryptionUtil> GetEncryptionUtil();
 
 	shared_ptr<AttachedDatabase> CreateAttachedDatabase(ClientContext &context, AttachInfo &info,
 	                                                    AttachOptions &options);
diff --git a/src/duckdb/src/include/duckdb/storage/storage_options.hpp b/src/duckdb/src/include/duckdb/storage/storage_options.hpp
index 786924b2c..4cf1f539b 100644
--- a/src/duckdb/src/include/duckdb/storage/storage_options.hpp
+++ b/src/duckdb/src/include/duckdb/storage/storage_options.hpp
@@ -40,11 +40,4 @@ struct StorageOptions {
 	void Initialize(const unordered_map<string, Value> &options);
 };
 
-inline void ClearUserKey(shared_ptr<string> const &encryption_key) {
-	if (encryption_key && !encryption_key->empty()) {
-		memset(&(*encryption_key)[0], 0, encryption_key->size());
-		encryption_key->clear();
-	}
-}
-
 } // namespace duckdb
diff --git a/src/duckdb/src/logging/log_manager.cpp b/src/duckdb/src/logging/log_manager.cpp
index 9a55dd280..07b31f7af 100644
--- a/src/duckdb/src/logging/log_manager.cpp
+++ b/src/duckdb/src/logging/log_manager.cpp
@@ -205,7 +205,7 @@ void LogManager::SetEnableStructuredLoggers(vector<string> &enabled_logger_types
 			throw InvalidInputException("Unknown log type: '%s'", enabled_logger_type);
 		}
 
-		new_config.enabled_log_types.insert(enabled_logger_type);
+		new_config.enabled_log_types.insert(lookup->name);
 
 		min_log_level = MinValue(min_log_level, lookup->level);
 	}
diff --git a/src/duckdb/src/main/database.cpp b/src/duckdb/src/main/database.cpp
index d7bb093eb..8d23656aa 100644
--- a/src/duckdb/src/main/database.cpp
+++ b/src/duckdb/src/main/database.cpp
@@ -507,12 +507,18 @@ SettingLookupResult DatabaseInstance::TryGetCurrentSetting(const string &key, Va
 	return db_config.TryGetCurrentSetting(key, result);
 }
 
-shared_ptr<EncryptionUtil> DatabaseInstance::GetEncryptionUtil() const {
+shared_ptr<EncryptionUtil> DatabaseInstance::GetEncryptionUtil() {
+	if (!config.encryption_util || !config.encryption_util->SupportsEncryption()) {
+		ExtensionHelper::TryAutoLoadExtension(*this, "httpfs");
+	}
+
 	if (config.encryption_util) {
 		return config.encryption_util;
 	}
 
-	return make_shared_ptr<duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLSFactory>();
+	auto result = make_shared_ptr<duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLSFactory>();
+
+	return std::move(result);
 }
 
 ValidChecker &DatabaseInstance::GetValidChecker() {
diff --git a/src/duckdb/src/main/http/http_util.cpp b/src/duckdb/src/main/http/http_util.cpp
index 85c5da463..fb5a9491f 100644
--- a/src/duckdb/src/main/http/http_util.cpp
+++ b/src/duckdb/src/main/http/http_util.cpp
@@ -130,9 +130,12 @@ BaseRequest::BaseRequest(RequestType type, const string &url, const HTTPHeaders
 class HTTPLibClient : public HTTPClient {
 public:
 	HTTPLibClient(HTTPParams &http_params, const string &proto_host_port) {
+		client = make_uniq<duckdb_httplib::Client>(proto_host_port);
+		Initialize(http_params);
+	}
+	void Initialize(HTTPParams &http_params) override {
 		auto sec = static_cast<time_t>(http_params.timeout);
 		auto usec = static_cast<time_t>(http_params.timeout_usec);
-		client = make_uniq<duckdb_httplib::Client>(proto_host_port);
 		client->set_follow_location(http_params.follow_location);
 		client->set_keep_alive(http_params.keep_alive);
 		client->set_write_timeout(sec, usec);
diff --git a/src/duckdb/src/storage/single_file_block_manager.cpp b/src/duckdb/src/storage/single_file_block_manager.cpp
index 42ebe4491..dc9c598cc 100644
--- a/src/duckdb/src/storage/single_file_block_manager.cpp
+++ b/src/duckdb/src/storage/single_file_block_manager.cpp
@@ -66,8 +66,8 @@ void DeserializeEncryptionData(ReadStream &stream, data_t *dest, idx_t size) {
 
 void GenerateDBIdentifier(uint8_t *db_identifier) {
 	memset(db_identifier, 0, MainHeader::DB_IDENTIFIER_LEN);
-	duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLS::GenerateRandomDataStatic(db_identifier,
-	                                                                          MainHeader::DB_IDENTIFIER_LEN);
+	RandomEngine engine;
+	engine.RandomData(db_identifier, MainHeader::DB_IDENTIFIER_LEN);
 }
 
 void EncryptCanary(MainHeader &main_header, const shared_ptr<EncryptionState> &encryption_state,
@@ -362,6 +362,15 @@ void SingleFileBlockManager::CheckAndAddEncryptionKey(MainHeader &main_header) {
 void SingleFileBlockManager::CreateNewDatabase(QueryContext context) {
 	auto flags = GetFileFlags(true);
 
+	auto encryption_enabled = options.encryption_options.encryption_enabled;
+	if (encryption_enabled) {
+		if (!db.GetDatabase().GetEncryptionUtil()->SupportsEncryption() && !options.read_only) {
+			throw InvalidConfigurationException(
+			    "The database was opened with encryption enabled, but DuckDB currently has a read-only crypto module "
+			    "loaded. Please re-open using READONLY, or ensure httpfs is loaded using `LOAD httpfs`.");
+		}
+	}
+
 	// open the RDBMS handle
 	auto &fs = FileSystem::Get(db);
 	handle = fs.OpenFile(path, flags);
@@ -376,7 +385,6 @@ void SingleFileBlockManager::CreateNewDatabase(QueryContext context) {
 	// Derive the encryption key and add it to the cache.
 	// Not used for plain databases.
 	data_t derived_key[MainHeader::DEFAULT_ENCRYPTION_KEY_LENGTH];
-	auto encryption_enabled = options.encryption_options.encryption_enabled;
 
 	// We need the unique database identifier, if the storage version is new enough.
 	// If encryption is enabled, we also use it as the salt.
@@ -487,6 +495,15 @@ void SingleFileBlockManager::LoadExistingDatabase(QueryContext context) {
 	if (main_header.IsEncrypted()) {
 		if (options.encryption_options.encryption_enabled) {
 			//! Encryption is set
+
+			//! Check if our encryption module can write, if not, we should throw here
+			if (!db.GetDatabase().GetEncryptionUtil()->SupportsEncryption() && !options.read_only) {
+				throw InvalidConfigurationException(
+				    "The database is encrypted, but DuckDB currently has a read-only crypto module loaded. Either "
+				    "re-open the database using `ATTACH '..' (READONLY)`, or ensure httpfs is loaded using `LOAD "
+				    "httpfs`.");
+			}
+
 			//! Check if the given key upon attach is correct
 			// Derive the encryption key and add it to cache
 			CheckAndAddEncryptionKey(main_header);
@@ -506,6 +523,19 @@ void SingleFileBlockManager::LoadExistingDatabase(QueryContext context) {
 			                       path, EncryptionTypes::CipherToString(config_cipher),
 			                       EncryptionTypes::CipherToString(stored_cipher));
 		}
+
+		// This avoids the cipher from being downgrades by an attacker FIXME: we likely want to have a propervalidation
+		// of the cipher used instead of this trick to avoid downgrades
+		if (stored_cipher != EncryptionTypes::GCM) {
+			if (config_cipher == EncryptionTypes::INVALID) {
+				throw CatalogException(
+				    "Cannot open encrypted database \"%s\" without explicitly specifying the "
+				    "encryption cipher for security reasons. Please make sure you understand the security implications "
+				    "and re-attach the database specifying the desired cipher.",
+				    path);
+			}
+		}
+
 		// this is ugly, but the storage manager does not know the cipher type before
 		db.GetStorageManager().SetCipher(stored_cipher);
 	}
diff --git a/src/duckdb/src/storage/storage_manager.cpp b/src/duckdb/src/storage/storage_manager.cpp
index ef90d5535..f0ce909c5 100644
--- a/src/duckdb/src/storage/storage_manager.cpp
+++ b/src/duckdb/src/storage/storage_manager.cpp
@@ -142,6 +142,14 @@ bool StorageManager::InMemory() const {
 	return path == IN_MEMORY_PATH;
 }
 
+inline void ClearUserKey(shared_ptr<string> const &encryption_key) {
+	if (encryption_key && !encryption_key->empty()) {
+		duckdb_mbedtls::MbedTlsWrapper::AESStateMBEDTLS::SecureClearData(data_ptr_cast(&(*encryption_key)[0]),
+		                                                                 encryption_key->size());
+		encryption_key->clear();
+	}
+}
+
 void StorageManager::Initialize(QueryContext context) {
 	bool in_memory = InMemory();
 	if (in_memory && read_only) {
diff --git a/src/duckdb/third_party/mbedtls/include/mbedtls_wrapper.hpp b/src/duckdb/third_party/mbedtls/include/mbedtls_wrapper.hpp
index d9f8111d8..e6e97a717 100644
--- a/src/duckdb/third_party/mbedtls/include/mbedtls_wrapper.hpp
+++ b/src/duckdb/third_party/mbedtls/include/mbedtls_wrapper.hpp
@@ -81,6 +81,7 @@ class AESStateMBEDTLS : public duckdb::EncryptionState {
 		DUCKDB_API void GenerateRandomData(duckdb::data_ptr_t data, duckdb::idx_t len) override;
 		DUCKDB_API void FinalizeGCM(duckdb::data_ptr_t tag, duckdb::idx_t tag_len);
 		DUCKDB_API const mbedtls_cipher_info_t *GetCipher(size_t key_len);
+		DUCKDB_API static void SecureClearData(duckdb::data_ptr_t data, duckdb::idx_t len);
 
 	private:
 		DUCKDB_API void InitializeInternal(duckdb::const_data_ptr_t iv, duckdb::idx_t iv_len, duckdb::const_data_ptr_t aad, duckdb::idx_t aad_len);
@@ -98,6 +99,10 @@ class AESStateMBEDTLS : public duckdb::EncryptionState {
 		}
 
 		~AESStateMBEDTLSFactory() override {} //
+
+		DUCKDB_API bool SupportsEncryption() override {
+			return false;
+		}
 	};
 };
 
diff --git a/src/duckdb/third_party/mbedtls/mbedtls_wrapper.cpp b/src/duckdb/third_party/mbedtls/mbedtls_wrapper.cpp
index 7dc0af7fd..3a6ce981e 100644
--- a/src/duckdb/third_party/mbedtls/mbedtls_wrapper.cpp
+++ b/src/duckdb/third_party/mbedtls/mbedtls_wrapper.cpp
@@ -271,6 +271,10 @@ const mbedtls_cipher_info_t *MbedTlsWrapper::AESStateMBEDTLS::GetCipher(size_t k
 	}
 }
 
+void MbedTlsWrapper::AESStateMBEDTLS::SecureClearData(duckdb::data_ptr_t data, duckdb::idx_t len) {
+	mbedtls_platform_zeroize(data, len);
+}
+
 MbedTlsWrapper::AESStateMBEDTLS::AESStateMBEDTLS(duckdb::EncryptionTypes::CipherType cipher_p, duckdb::idx_t key_len) : EncryptionState(cipher_p, key_len), context(duckdb::make_uniq<mbedtls_cipher_context_t>()) {
 	mbedtls_cipher_init(context.get());
 
@@ -296,20 +300,12 @@ MbedTlsWrapper::AESStateMBEDTLS::~AESStateMBEDTLS() {
 	}
 }
 
-void MbedTlsWrapper::AESStateMBEDTLS::GenerateRandomDataStatic(duckdb::data_ptr_t data, duckdb::idx_t len) {
-	duckdb::RandomEngine random_engine;
-
-	while (len) {
-		const auto random_integer = random_engine.NextRandomInteger();
-		const auto next = duckdb::MinValue<duckdb::idx_t>(len, sizeof(random_integer));
-		memcpy(data, duckdb::const_data_ptr_cast(&random_integer), next);
-		data += next;
-		len -= next;
-	}
+static void ThrowInsecureRNG() {
+	throw duckdb::InvalidConfigurationException("DuckDB requires a secure random engine to be loaded to enable secure crypto. Normally, this will be handled automatically by DuckDB by autoloading the `httpfs` Extension, but that seems to have failed. Please ensure the httpfs extension is loaded manually using `LOAD httpfs`.");
 }
 
 void MbedTlsWrapper::AESStateMBEDTLS::GenerateRandomData(duckdb::data_ptr_t data, duckdb::idx_t len) {
-	GenerateRandomDataStatic(data, len);
+	ThrowInsecureRNG();
 }
 
 void MbedTlsWrapper::AESStateMBEDTLS::InitializeInternal(duckdb::const_data_ptr_t iv, duckdb::idx_t iv_len, duckdb::const_data_ptr_t aad, duckdb::idx_t aad_len){
@@ -325,16 +321,7 @@ void MbedTlsWrapper::AESStateMBEDTLS::InitializeInternal(duckdb::const_data_ptr_
 }
 
 void MbedTlsWrapper::AESStateMBEDTLS::InitializeEncryption(duckdb::const_data_ptr_t iv, duckdb::idx_t iv_len, duckdb::const_data_ptr_t key, duckdb::idx_t key_len_p, duckdb::const_data_ptr_t aad, duckdb::idx_t aad_len) {
-	mode = duckdb::EncryptionTypes::ENCRYPT;
-
-	if (key_len_p != key_len) {
-		throw duckdb::InternalException("Invalid encryption key length, expected %llu, got %llu", key_len, key_len_p);
-	}
-	if (mbedtls_cipher_setkey(context.get(), key, key_len * 8, MBEDTLS_ENCRYPT)) {
-		throw runtime_error("Failed to set AES key for encryption");
-	}
-
-	InitializeInternal(iv, iv_len, aad, aad_len);
+	ThrowInsecureRNG();
 }
 
 void MbedTlsWrapper::AESStateMBEDTLS::InitializeDecryption(duckdb::const_data_ptr_t iv, duckdb::idx_t iv_len, duckdb::const_data_ptr_t key, duckdb::idx_t key_len_p, duckdb::const_data_ptr_t aad, duckdb::idx_t aad_len) {