diff --git a/src/chainloader/utils.cpp b/src/chainloader/utils.cpp
index 4e36bdd6..ccd65d33 100644
--- a/src/chainloader/utils.cpp
+++ b/src/chainloader/utils.cpp
@@ -104,3 +104,23 @@ void* find_plugin_library(const std::string& name) {
 
     return handle;
 }
+
+void log_failing_dlsym(const std::string& library_name,
+                       const char* function_name) {
+    const fs::path this_plugin_path = get_this_file_location();
+
+    Logger logger = Logger::create_exception_logger();
+
+    logger.log("");
+    logger.log("Could not find '" + std::string(function_name) + "' in '" +
+               library_name + "'");
+    logger.log("");
+    logger.log("Try rerunning 'yabridgectl sync'.");
+    logger.log("");
+    logger.log("Source: '" + this_plugin_path.string() + "'");
+    logger.log("");
+
+    send_notification("Could not find '" + std::string(function_name) +
+                          "' in '" + library_name + "'",
+                      "Try rerunning 'yabridgectl sync'.", this_plugin_path);
+}
diff --git a/src/chainloader/utils.h b/src/chainloader/utils.h
index 0bd2c769..b572eb3d 100644
--- a/src/chainloader/utils.h
+++ b/src/chainloader/utils.h
@@ -37,3 +37,10 @@
  *   directories in case `ldconfig` was not set up correctly.
  */
 void* find_plugin_library(const std::string& name);
+
+/**
+ * Log a message when a `dlsym()` call fails and show a corresponding desktop
+ * notification. Used as part of the `LOAD_FUNCTION` macros.
+ */
+void log_failing_dlsym(const std::string& library_name,
+                       const char* function_name);
diff --git a/src/chainloader/vst2-chainloader.cpp b/src/chainloader/vst2-chainloader.cpp
index 030bebaf..2078fde5 100644
--- a/src/chainloader/vst2-chainloader.cpp
+++ b/src/chainloader/vst2-chainloader.cpp
@@ -76,7 +76,10 @@ bool initialize_library() {
     do {                                                                    \
         (name) =                                                            \
             reinterpret_cast<decltype(name)>(dlsym(library_handle, #name)); \
-        assert(name);                                                       \
+        if (!(name)) {                                                      \
+            log_failing_dlsym(yabridge_vst2_plugin_name, #name);            \
+            return false;                                                   \
+        }                                                                   \
     } while (false)
 
     LOAD_FUNCTION(yabridge_plugin_init);
diff --git a/src/chainloader/vst3-chainloader.cpp b/src/chainloader/vst3-chainloader.cpp
index 3ce91113..103084c5 100644
--- a/src/chainloader/vst3-chainloader.cpp
+++ b/src/chainloader/vst3-chainloader.cpp
@@ -94,7 +94,10 @@ bool initialize_library() {
     do {                                                                    \
         (name) =                                                            \
             reinterpret_cast<decltype(name)>(dlsym(library_handle, #name)); \
-        assert(name);                                                       \
+        if (!(name)) {                                                      \
+            log_failing_dlsym(yabridge_vst3_plugin_name, #name);            \
+            return false;                                                   \
+        }                                                                   \
     } while (false)
 
     LOAD_FUNCTION(yabridge_module_init);