diff --git a/plugin-core/src/main/java/appland/cli/FailedDownloadNotificationListener.java b/plugin-core/src/main/java/appland/cli/FailedDownloadNotificationListener.java
new file mode 100644
index 00000000..0767c9c0
--- /dev/null
+++ b/plugin-core/src/main/java/appland/cli/FailedDownloadNotificationListener.java
@@ -0,0 +1,20 @@
+package appland.cli;
+
+import appland.notifications.AppMapNotifications;
+import com.intellij.openapi.project.Project;
+import org.jetbrains.annotations.NotNull;
+
+public final class FailedDownloadNotificationListener implements AppLandDownloadListener {
+    @NotNull private final Project project;
+
+    public FailedDownloadNotificationListener(@NotNull Project project) {
+        this.project = project;
+    }
+
+    @Override
+    public void downloadFinished(@NotNull CliTool type, boolean success) {
+        if (!success) {
+            AppMapNotifications.showFailedCliBinaryDownloadNotification(project);
+        }
+    }
+}
diff --git a/plugin-core/src/main/java/appland/notifications/AppMapNotifications.java b/plugin-core/src/main/java/appland/notifications/AppMapNotifications.java
index 611e7c56..2044e76f 100644
--- a/plugin-core/src/main/java/appland/notifications/AppMapNotifications.java
+++ b/plugin-core/src/main/java/appland/notifications/AppMapNotifications.java
@@ -354,4 +354,36 @@ public static void showCopilotAuthenticationRequired() {
             }
         });
     }
+
+    /**
+     * See https://github.com/getappmap/appmap-intellij-plugin/issues/814.
+     */
+    public static void showFailedCliBinaryDownloadNotification(@NotNull Project project) {
+        if (!AppMapApplicationSettingsService.getInstance().isShowFailedCliDownloadError()) {
+            return;
+        }
+
+        // the message should only appear once
+        AppMapApplicationSettingsService.getInstance().setShowFailedCliDownloadError(false);
+
+        ApplicationManager.getApplication().invokeLater(() -> {
+            Notification notification = new AppMapFullContentNotification(
+                    GENERIC_NOTIFICATIONS_ID,
+                    null,
+                    AppMapBundle.get("notification.cliDownloadFailed.title"),
+                    null,
+                    AppMapBundle.get("notification.cliDownloadFailed.content"),
+                    NotificationType.ERROR,
+                    null
+            );
+
+            var showInstructionsAction = NotificationAction.create(lazy("notification.cliDownloadFailed.browseAction"), (e, n) -> {
+                n.expire();
+                BrowserUtil.browse("https://appmap.io/docs/reference/appmap-airgapped-install.html#download-the-appmap-application-binaries");
+            });
+
+            notification = notification.addAction(showInstructionsAction);
+            notification.notify(project);
+        });
+    }
 }
diff --git a/plugin-core/src/main/java/appland/settings/AppMapApplicationSettings.java b/plugin-core/src/main/java/appland/settings/AppMapApplicationSettings.java
index cc045751..d19ca7d8 100644
--- a/plugin-core/src/main/java/appland/settings/AppMapApplicationSettings.java
+++ b/plugin-core/src/main/java/appland/settings/AppMapApplicationSettings.java
@@ -65,6 +65,8 @@ public class AppMapApplicationSettings {
      */
     private volatile int maxPinnedFileSizeKB = 20;
 
+    private volatile boolean showFailedCliDownloadError = true;
+
     public AppMapApplicationSettings() {
     }
 
diff --git a/plugin-core/src/main/resources/META-INF/appmap-core.xml b/plugin-core/src/main/resources/META-INF/appmap-core.xml
index c1057a69..4674c876 100644
--- a/plugin-core/src/main/resources/META-INF/appmap-core.xml
+++ b/plugin-core/src/main/resources/META-INF/appmap-core.xml
@@ -24,6 +24,9 @@
         <listener topic="appland.cli.AppLandDownloadListener"
                   class="appland.cli.StartServicesAfterDownloadListener"/>
 
+        <listener topic="appland.cli.AppLandDownloadListener"
+                  class="appland.cli.FailedDownloadNotificationListener"/>
+
         <listener topic="appland.files.AppMapFileChangeListener"
                   class="appland.notifications.FirstAppMapListener"/>
     </projectListeners>
diff --git a/plugin-core/src/main/resources/messages/appland.properties b/plugin-core/src/main/resources/messages/appland.properties
index 33846a77..0b49f5ac 100644
--- a/plugin-core/src/main/resources/messages/appland.properties
+++ b/plugin-core/src/main/resources/messages/appland.properties
@@ -122,6 +122,7 @@ dirPathValidation.notDir=Please enter the location of a directory, not a file.
 
 nameValidation.empty=Please enter a valid name.
 
+notification.dontShowAgainOption=Don't show again
 notification.closeButton=Close
 notification.stopButton=Stop
 notification.recordingHelpButton=Show Help
@@ -162,6 +163,10 @@ notification.exportAppMapJson.content=An error occurred while exporting AppMap J
 
 notification.reloadProject.content=Please reload your project because the AppMap settings changed.
 
+notification.cliDownloadFailed.title=Download Failed: AppMap CLI Tools
+notification.cliDownloadFailed.content=Failed to download the AppMap CLI tools. This is a required dependency of the AppMap plugin. Please refer to the instructions to manually install it.
+notification.cliDownloadFailed.browseAction=Show instructions
+
 statusBar.recording.displayName=AppMap Recording
 statusBar.recording.recordingStatus=Recording...