diff --git a/src/main/java/ai/reveng/toolkit/ghidra/core/tasks/StartAnalysisTask.java b/src/main/java/ai/reveng/toolkit/ghidra/core/tasks/StartAnalysisTask.java
index 8e4d41a5..8296937f 100644
--- a/src/main/java/ai/reveng/toolkit/ghidra/core/tasks/StartAnalysisTask.java
+++ b/src/main/java/ai/reveng/toolkit/ghidra/core/tasks/StartAnalysisTask.java
@@ -6,8 +6,11 @@
 import ai.reveng.toolkit.ghidra.core.services.api.AnalysisOptionsBuilder;
 import ai.reveng.toolkit.ghidra.core.services.api.GhidraRevengService;
 import ai.reveng.toolkit.ghidra.core.services.api.types.AnalysisStatus;
+import ai.reveng.toolkit.ghidra.core.services.logging.ReaiLoggingService;
+import ai.reveng.toolkit.ghidra.plugins.ReaiPluginPackage;
 import ghidra.framework.plugintool.PluginTool;
 import ghidra.program.model.listing.Program;
+import ghidra.util.Msg;
 import ghidra.util.exception.CancelledException;
 import ghidra.util.task.Task;
 import ghidra.util.task.TaskMonitor;
@@ -42,20 +45,35 @@ public StartAnalysisTask(Program program,
 
     @Override
     public void run(TaskMonitor monitor) throws CancelledException {
+        ReaiLoggingService loggingService = tool.getService(ReaiLoggingService.class);
+
         monitor.setMessage("Uploading Binary");
-        reService.upload(program);
-        monitor.setMessage("Exporting Function Boundaries");
+        try {
+            reService.upload(program);
+        } catch (RuntimeException e) {
+            reportFailure(monitor, loggingService, "Failed to upload binary", e);
+            return;
+        }
 
         monitor.setMessage("Sending Analysis Request");
-
         GhidraRevengService.ProgramWithID programWithID;
         try {
-        programWithID = reService.startAnalysis(program, options);
+            programWithID = reService.startAnalysis(program, options);
         } catch (ApiException e) {
-            monitor.setMessage("Analysis Request Failed");
+            reportFailure(monitor, loggingService, "Analysis request was rejected by the server", e);
+            return;
+        } catch (RuntimeException e) {
+            reportFailure(monitor, loggingService, "Failed to start analysis", e);
             return;
         }
 
+        String successMessage = "Analysis started successfully (analysis ID %s)"
+                .formatted(programWithID.analysisID().id());
+        monitor.setMessage(successMessage);
+        if (loggingService != null) {
+            loggingService.info(successMessage);
+        }
+
         tool.firePluginEvent(new RevEngAIAnalysisStatusChangedEvent(
                 "StartAnalysisTask",
                 programWithID,
@@ -63,6 +81,34 @@ public void run(TaskMonitor monitor) throws CancelledException {
         );
     }
 
+    private void reportFailure(TaskMonitor monitor,
+                               ReaiLoggingService loggingService,
+                               String context,
+                               Throwable error) {
+        String message = context + ": " + describe(error);
+        monitor.setMessage("Analysis Request Failed");
+        if (loggingService != null) {
+            loggingService.error(message);
+        }
+        Msg.error(this, message, error);
+        Msg.showError(this, null,
+                ReaiPluginPackage.WINDOW_PREFIX + "Failed to start analysis",
+                message, error);
+    }
+
+    private static String describe(Throwable error) {
+        Throwable cause = error;
+        if (!(cause instanceof ApiException) && cause.getCause() instanceof ApiException) {
+            cause = cause.getCause();
+        }
+        if (cause instanceof ApiException apiException) {
+            String body = apiException.getResponseBody();
+            String detail = (body != null && !body.isBlank()) ? body : apiException.getMessage();
+            return "HTTP " + apiException.getCode() + " — " + detail;
+        }
+        return cause.getMessage() != null ? cause.getMessage() : cause.toString();
+    }
+
     @Override
     public boolean getWaitForTaskCompleted() {
         return super.getWaitForTaskCompleted();
diff --git a/src/main/java/ai/reveng/toolkit/ghidra/plugins/AnalysisManagementPlugin.java b/src/main/java/ai/reveng/toolkit/ghidra/plugins/AnalysisManagementPlugin.java
index 2573bf71..cda6bea0 100644
--- a/src/main/java/ai/reveng/toolkit/ghidra/plugins/AnalysisManagementPlugin.java
+++ b/src/main/java/ai/reveng/toolkit/ghidra/plugins/AnalysisManagementPlugin.java
@@ -151,9 +151,10 @@ private void setupActions() {
                         var builder = TaskBuilder.withTask(task);
                         analysisLogComponent.setVisible(true);
                         builder.launchInBackground(analysisLogComponent.getTaskMonitor());
-                        // The task will fire the RevEngAIAnalysisStatusChangedEvent event when done
-                        // which is then picked up by the AnalysisManagementPlugin and forwarded to the AnalysisLogComponent
-                        tool.getService(ReaiLoggingService.class).info("Started analysis: ");
+                        // The task runs in the background and logs the actual outcome (success or failure)
+                        // itself. On success it fires the RevEngAIAnalysisStatusChangedEvent, which is picked
+                        // up by the AnalysisManagementPlugin and forwarded to the AnalysisLogComponent.
+                        tool.getService(ReaiLoggingService.class).info("Launching analysis task in background");
                     } else {
                         // User clicked Cancel
                         tool.getService(ReaiLoggingService.class).info("Create new analysis dialog cancelled by user");