diff --git a/CHANGELOG.md b/CHANGELOG.md
index 883250bd..03fd8b0e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -23,6 +23,9 @@ Versioning](https://semver.org/spec/v2.0.0.html).
   of only printing it to the logger. This makes diagnosing issues much faster if
   you didn't already start your DAW from a terminal. These notifications require
   `libnotify` and the `notify-send` application to be installed.
+- Also added a warning and a desktop notification when there's a version
+  mismatch between the yabridge host application and the plugin to remind you to
+  rerun `yabridgectl sync`.
 - Added an environment variable to disable the watchdog timer. This allows the
   Wine process to run under a separate namespace. If you don't know that you
   need this, then you probably don't need this!
diff --git a/src/common/serialization/vst3.h b/src/common/serialization/vst3.h
index 09779134..c8baa61b 100644
--- a/src/common/serialization/vst3.h
+++ b/src/common/serialization/vst3.h
@@ -51,13 +51,19 @@
 
 /**
  * Marker struct to indicate the other side (the plugin) should send a copy of
- * the configuration.
+ * the configuration. During this process we will also transmit the version
+ * string from the host, so we can show a little warning when the user forgot to
+ * rerun `yabridgectl sync` (and the initialization was still successful).
  */
 struct WantsConfiguration {
     using Response = Configuration;
 
+    std::string host_version;
+
     template <typename S>
-    void serialize(S&) {}
+    void serialize(S& s) {
+        s.text1b(host_version, 128);
+    }
 };
 
 /**
diff --git a/src/plugin/bridges/common.h b/src/plugin/bridges/common.h
index fc4b555e..9bd4218e 100644
--- a/src/plugin/bridges/common.h
+++ b/src/plugin/bridges/common.h
@@ -339,6 +339,30 @@ class PluginBridge {
 #endif
     }
 
+    /**
+     * Show a desktop notification if the Wine plugin host is using a different
+     * version of yabridge than this library. Yabridge may still work (and we do
+     * this often during development), but at some point a request may fail the
+     * plugin and the host are out of sync.
+     */
+    void warn_on_version_mismatch(const std::string& host_version) {
+        if (host_version != yabridge_git_version) {
+            generic_logger.log(
+                "WARNING: The host application's version does not match");
+            generic_logger.log(
+                "         this plugin's. If you just updated yabridge, then");
+            generic_logger.log(
+                "         you may need rerun 'yabridgectl sync' first to");
+            generic_logger.log("         update your plugins.");
+
+            send_notification(
+                "Version mismatch",
+                "If you just updated yabridge, then you may need "
+                "to rerun 'yabridgectl sync' first to update your plugins.",
+                true);
+        }
+    }
+
     /**
      * The configuration for this instance of yabridge. Set based on the values
      * from a `yabridge.toml`, if it exists.
diff --git a/src/plugin/bridges/vst3.cpp b/src/plugin/bridges/vst3.cpp
index 3fdb5df1..ddcb27d8 100644
--- a/src/plugin/bridges/vst3.cpp
+++ b/src/plugin/bridges/vst3.cpp
@@ -63,7 +63,10 @@ Vst3PluginBridge::Vst3PluginBridge()
 
                     return Ack{};
                 },
-                [&](const WantsConfiguration&) -> WantsConfiguration::Response {
+                [&](const WantsConfiguration& request)
+                    -> WantsConfiguration::Response {
+                    warn_on_version_mismatch(request.host_version);
+
                     return config;
                 },
                 [&](const YaComponentHandler::BeginEdit& request)
diff --git a/src/wine-host/bridges/vst3.cpp b/src/wine-host/bridges/vst3.cpp
index 8531e30f..db7928e7 100644
--- a/src/wine-host/bridges/vst3.cpp
+++ b/src/wine-host/bridges/vst3.cpp
@@ -24,6 +24,9 @@
 #include "vst3-impls/host-context-proxy.h"
 #include "vst3-impls/plug-frame-proxy.h"
 
+// Generated inside of the build directory
+#include <version.h>
+
 // NOLINTNEXTLINE(bugprone-suspicious-include)
 #include <public.sdk/source/vst/hosting/module_win32.cpp>
 
@@ -100,8 +103,8 @@ Vst3Bridge::Vst3Bridge(MainContext& main_context,
 
     // Fetch this instance's configuration from the plugin to finish the setup
     // process
-    config = sockets.vst_host_callback.send_message(WantsConfiguration{},
-                                                    std::nullopt);
+    config = sockets.vst_host_callback.send_message(
+        WantsConfiguration{.host_version = yabridge_git_version}, std::nullopt);
 
     // Allow this plugin to configure the main context's tick rate
     main_context.update_timer_interval(config.event_loop_interval());