diff --git a/sqlite3/assets/wasm/CMakeLists.txt b/sqlite3/assets/wasm/CMakeLists.txt
index 71f5a747..3cdb4717 100644
--- a/sqlite3/assets/wasm/CMakeLists.txt
+++ b/sqlite3/assets/wasm/CMakeLists.txt
@@ -12,7 +12,7 @@ include(FetchContent)
 FetchContent_Declare(
     sqlite3
     # NOTE: When changing this, also update `test/wasm/sqlite3_test.dart`
-    URL https://sqlite.org/2024/sqlite-autoconf-3470200.tar.gz
+    URL https://github.com/utelle/SQLite3MultipleCiphers/releases/download/v1.9.2/sqlite3mc-1.9.2-sqlite-3.47.2-amalgamation.zip
     DOWNLOAD_EXTRACT_TIMESTAMP NEW
 )
 
@@ -38,13 +38,13 @@ macro(base_sqlite3_target name debug)
   set(sources
     ${CMAKE_CURRENT_SOURCE_DIR}/os_web.c
     ${CMAKE_CURRENT_SOURCE_DIR}/helpers.c
-    ${sqlite3_SOURCE_DIR}/sqlite3.c
+    ${sqlite3_SOURCE_DIR}/sqlite3mc_amalgamation.c
   )
   set(flags -Wall -Wextra -Wno-unused-parameter -Wno-unused-function)
 
   if(${debug})
     list(APPEND sources "${CMAKE_BINARY_DIR}/vfstrace.c")
-    list(APPEND flags "-g" "-DDEBUG")
+    list(APPEND flags "-g" "-DDEBUG" "-O1")
   else()
     list(APPEND flags "-Oz" "-DNDEBUG" "-flto")
   endif()
@@ -56,6 +56,8 @@ macro(base_sqlite3_target name debug)
       -o ${clang_output}
       -I ${PROJECT_SOURCE_DIR} -I ${sqlite3_SOURCE_DIR}
       -D_HAVE_SQLITE_CONFIG_H
+      -DSQLITE_OMIT_AUTOINIT
+      -D__WASM__
       -mcpu=generic
       -mexec-model=reactor
       -fno-stack-protector -fno-stack-clash-protection
diff --git a/sqlite3/assets/wasm/helpers.c b/sqlite3/assets/wasm/helpers.c
index 380104ca..90b4e992 100644
--- a/sqlite3/assets/wasm/helpers.c
+++ b/sqlite3/assets/wasm/helpers.c
@@ -187,7 +187,11 @@ SQLITE_API sqlite3_vfs *dart_sqlite3_register_vfs(const char *name, int dartId,
   vfstrace_register(traceName, name, &dartvfs_trace_log1, NULL, makeDefault);
 #else
   // Just register the VFS as is.
-  sqlite3_vfs_register(vfs, makeDefault);
+  int rc = sqlite3_vfs_register(vfs, makeDefault);
+  if (rc) {
+    free(vfs);
+    return NULL;
+  }
 #endif
   return vfs;
 }
diff --git a/sqlite3/assets/wasm/os_web.c b/sqlite3/assets/wasm/os_web.c
index 98004432..35e6db42 100644
--- a/sqlite3/assets/wasm/os_web.c
+++ b/sqlite3/assets/wasm/os_web.c
@@ -5,6 +5,15 @@
 #include "bridge.h"
 #include "sqlite3.h"
 
-int sqlite3_os_init(void) { return SQLITE_OK; }
+extern int sqlite3_powersync_init(sqlite3 *db, char **pzErrMsg,
+                                  const sqlite3_api_routines *pApi);
+
+int getentropy(void* buf, size_t n) {
+    return xRandomness(-1, (int) n, (char*) buf);
+}
+
+int sqlite3_os_init(void) {
+    return SQLITE_OK;
+}
 
 int sqlite3_os_end(void) { return SQLITE_OK; }
diff --git a/sqlite3/example/web/main.dart b/sqlite3/example/web/main.dart
index f7bf0bfc..9adb623c 100644
--- a/sqlite3/example/web/main.dart
+++ b/sqlite3/example/web/main.dart
@@ -15,11 +15,12 @@ Future<void> main() async {
     print(sqlite3.version);
 
     sqlite3.registerVirtualFileSystem(
-      await IndexedDbFileSystem.open(dbName: 'sqlite3-example'),
+      InMemoryFileSystem(),
       makeDefault: true,
     );
 
-    sqlite3.open('/database')
+    sqlite3.open('/database', vfs: 'multipleciphers-dart-memory')
+      ..execute("pragma key = 'test';")
       ..execute('pragma user_version = 1')
       ..execute('CREATE TABLE foo (bar INTEGER NOT NULL);')
       ..execute('INSERT INTO foo (bar) VALUES (?)', [3])
diff --git a/sqlite3/lib/src/vfs.dart b/sqlite3/lib/src/vfs.dart
index 7cad5883..88395584 100644
--- a/sqlite3/lib/src/vfs.dart
+++ b/sqlite3/lib/src/vfs.dart
@@ -132,18 +132,30 @@ abstract base class BaseVirtualFileSystem extends VirtualFileSystem {
   final Random random;
 
   BaseVirtualFileSystem({Random? random, required String name})
-      : random = random ?? Random.secure(),
+      : random = random ?? _fallbackRandom,
         super(name);
 
   @override
   void xRandomness(Uint8List target) {
+    generateRandomness(target, random);
+  }
+
+  @override
+  DateTime xCurrentTime() => DateTime.now();
+
+  /// Fills [target] with random bytes.
+  ///
+  /// An optional [random] source can be provided, otherwise a default instance
+  /// of [Random.secure] will be used.
+  static void generateRandomness(Uint8List target, [Random? random]) {
+    random ??= _fallbackRandom;
+
     for (var i = 0; i < target.length; i++) {
       target[i] = random.nextInt(1 << 8);
     }
   }
 
-  @override
-  DateTime xCurrentTime() => DateTime.now();
+  static final Random _fallbackRandom = Random.secure();
 }
 
 /// A [VirtualFileSystemFile] base class that implements [xRead] to zero-fill
diff --git a/sqlite3/lib/src/wasm/bindings.dart b/sqlite3/lib/src/wasm/bindings.dart
index f6245d2d..bf210817 100644
--- a/sqlite3/lib/src/wasm/bindings.dart
+++ b/sqlite3/lib/src/wasm/bindings.dart
@@ -5,6 +5,7 @@ import 'dart:typed_data';
 import 'package:sqlite3/src/vfs.dart';
 
 import '../constants.dart';
+import '../exception.dart';
 import '../functions.dart';
 import '../implementation/bindings.dart';
 import 'wasm_interop.dart' as wasm;
@@ -55,6 +56,8 @@ final class WasmSqliteBindings extends RawSqliteBindings {
   @override
   SqliteResult<RawSqliteDatabase> sqlite3_open_v2(
       String name, int flags, String? zVfs) {
+    sqlite3_initialize();
+
     final namePtr = bindings.allocateZeroTerminated(name);
     final outDb = bindings.malloc(wasm.WasmBindings.pointerSize);
     final vfsPtr = zVfs == null ? 0 : bindings.allocateZeroTerminated(zVfs);
@@ -76,12 +79,23 @@ final class WasmSqliteBindings extends RawSqliteBindings {
     return bindings.memory.readString(bindings.sqlite3_sourceid());
   }
 
+  void sqlite3_initialize() {
+    final rc = bindings.sqlite3_initialize();
+    if (rc != 0) {
+      throw SqliteException(rc, 'sqlite3_initialize call failed');
+    }
+  }
+
   @override
   void registerVirtualFileSystem(VirtualFileSystem vfs, int makeDefault) {
     final name = bindings.allocateZeroTerminated(vfs.name);
     final id = bindings.callbacks.registerVfs(vfs);
 
     final ptr = bindings.dart_sqlite3_register_vfs(name, id, makeDefault);
+    if (ptr == 0) {
+      throw StateError('could not register vfs');
+    }
+    sqlite3_initialize();
     DartCallbacks.sqliteVfsPointer[vfs] = ptr;
   }
 
diff --git a/sqlite3/lib/src/wasm/wasm_interop.dart b/sqlite3/lib/src/wasm/wasm_interop.dart
index 75a1ca94..1f9d1d68 100644
--- a/sqlite3/lib/src/wasm/wasm_interop.dart
+++ b/sqlite3/lib/src/wasm/wasm_interop.dart
@@ -83,7 +83,7 @@ class WasmBindings {
       _sqlite3_stmt_readonly,
       _sqlite3_stmt_isexplain;
 
-  final JSFunction? _sqlite3_db_config;
+  final JSFunction? _sqlite3_db_config, _sqlite3_initialize;
 
   final Global _sqlite3_temp_directory;
 
@@ -160,7 +160,9 @@ class WasmBindings {
         _sqlite3_stmt_isexplain = instance.functions['sqlite3_stmt_isexplain']!,
         _sqlite3_stmt_readonly = instance.functions['sqlite3_stmt_readonly']!,
         _sqlite3_db_config = instance.functions['dart_sqlite3_db_config_int'],
+        _sqlite3_initialize = instance.functions['sqlite3_initialize'],
         _sqlite3_temp_directory = instance.globals['sqlite3_temp_directory']!
+
   // Note when adding new fields: We remove functions from the wasm module that
   // aren't referenced in Dart. We consider a symbol used when it appears in a
   // string literal in an initializer of this constructor (`tool/wasm_dce.dart`).
@@ -210,6 +212,13 @@ class WasmBindings {
 
   void sqlite3_free(Pointer ptr) => _sqlite3_free.callReturningVoid(ptr.toJS);
 
+  int sqlite3_initialize() {
+    return switch (_sqlite3_initialize) {
+      final fun? => fun.callReturningInt0(),
+      null => 0,
+    };
+  }
+
   int create_scalar_function(
       Pointer db, Pointer functionName, int nArg, int eTextRep, int id) {
     return _create_scalar.callReturningInt5(
@@ -601,10 +610,18 @@ class _InjectedValues {
           });
         }).toJS,
         'xRandomness': ((int vfsId, int nByte, Pointer zOut) {
-          final vfs = callbacks.registeredVfs[vfsId]!;
+          final vfs = callbacks.registeredVfs[vfsId];
 
           return _runVfs(() {
-            vfs.xRandomness(memory.buffer.toDart.asUint8List(zOut, nByte));
+            final target = memory.buffer.toDart.asUint8List(zOut, nByte);
+
+            if (vfs != null) {
+              vfs.xRandomness(target);
+            } else {
+              // Fall back to a default random source. We're using this to
+              // implement `getentropy` in C which is used by sqlite3mc.
+              return BaseVirtualFileSystem.generateRandomness(target);
+            }
           });
         }).toJS,
         'xSleep': ((int vfsId, int micros) {