diff --git a/lib/sentry_dart_plugin.dart b/lib/sentry_dart_plugin.dart
index a69463d7..aa3fac63 100644
--- a/lib/sentry_dart_plugin.dart
+++ b/lib/sentry_dart_plugin.dart
@@ -60,6 +60,8 @@ class SentryDartPlugin {
       await _executeFinalizeRelease(release);
     } on ExitError catch (e) {
       return e.code;
+    } finally {
+      Log.tasksSummary();
     }
     return 0;
   }
@@ -187,13 +189,27 @@ class SentryDartPlugin {
   }
 
   Future<void> _executeNewRelease(String release) async {
-    await _executeAndLog('Failed to create a new release',
+    final taskName = 'create new release: $release';
+    Log.startingTask(taskName);
+    final isSuccess = await _executeAndLog('Failed to create a new release',
         [..._releasesCliParams(), 'new', release]);
+    if (isSuccess) {
+      Log.taskCompleted(taskName);
+    } else {
+      Log.taskSkipped(taskName);
+    }
   }
 
   Future<void> _executeFinalizeRelease(String release) async {
-    await _executeAndLog('Failed to finalize the new release',
+    final taskName = 'finalize new release: $release';
+    Log.startingTask(taskName);
+    final isSuccess = await _executeAndLog('Failed to finalize the new release',
         [..._releasesCliParams(), 'finalize', release]);
+    if (isSuccess) {
+      Log.taskCompleted(taskName);
+    } else {
+      Log.taskSkipped(taskName);
+    }
   }
 
   Future<void> _executeSetCommits(String release) async {
@@ -214,7 +230,14 @@ class SentryDartPlugin {
       params.add('--ignore-missing');
     }
 
-    await _executeAndLog('Failed to set commits', params);
+    final taskName = 'set commits';
+    Log.startingTask(taskName);
+    final isSuccess = await _executeAndLog('Failed to set commits', params);
+    if (isSuccess) {
+      Log.taskCompleted(taskName);
+    } else {
+      Log.taskSkipped(taskName);
+    }
   }
 
   Future<List<String>> _findAllJsFilePaths() async {
@@ -280,7 +303,7 @@ class SentryDartPlugin {
     return await _executeAndLog('Failed to inject debug ids', params);
   }
 
-  Future<void> _uploadSourceMaps(
+  Future<bool> _uploadSourceMaps(
       {required String release, required String? dist}) async {
     List<String> params = [];
 
@@ -325,7 +348,7 @@ class SentryDartPlugin {
 
     params.addAll(_baseCliParams());
 
-    await _executeAndLog('Failed to sources files', params);
+    return await _executeAndLog('Failed to sources files', params);
   }
 
   /// Extracts and returns a list of path prefixes to strip from source maps.
@@ -417,7 +440,7 @@ class SentryDartPlugin {
       }
     }
 
-    const taskName = 'uploading source maps';
+    const taskName = 'uploading source maps (legacy)';
     Log.startingTask(taskName);
 
     final params = <String>[];
@@ -440,7 +463,13 @@ class SentryDartPlugin {
     _addWait(releaseJsFilesParams);
     _addUrlPrefix(releaseJsFilesParams);
 
-    await _executeAndLog('Failed to upload source maps', releaseJsFilesParams);
+    final isSourcemapsUploadSuccessful = await _executeAndLog(
+        'Failed to upload source maps', releaseJsFilesParams);
+    if (!isSourcemapsUploadSuccessful) {
+      Log.taskSkipped(taskName);
+      // no need to continue if it was a failure
+      return;
+    }
 
     if (_configuration.uploadSources) {
       // upload source files (dart)
@@ -457,8 +486,13 @@ class SentryDartPlugin {
 
       _addWait(releaseDartFilesParams);
 
-      await _executeAndLog(
+      final isSourcesUploadSuccessful = await _executeAndLog(
           'Failed to upload source files', releaseDartFilesParams);
+      if (!isSourcesUploadSuccessful) {
+        Log.taskSkipped(taskName);
+        // no need to continue if it was a failure
+        return;
+      }
     }
 
     Log.taskCompleted(taskName);
@@ -471,12 +505,16 @@ class SentryDartPlugin {
 
     final debugIdInjectionSucceeded = await _injectDebugIds();
     if (debugIdInjectionSucceeded) {
-      await _uploadSourceMaps(release: release, dist: dist);
+      final isSuccess = await _uploadSourceMaps(release: release, dist: dist);
+      if (isSuccess) {
+        Log.taskCompleted(taskName);
+      } else {
+        Log.taskSkipped(taskName);
+      }
     } else {
       Log.warn('Skipping source maps upload. Could not inject debug ids.');
+      Log.taskSkipped(taskName);
     }
-
-    Log.taskCompleted(taskName);
   }
 
   void _addUrlPrefix(List<String> releaseDartFilesParams) {
diff --git a/lib/src/utils/log.dart b/lib/src/utils/log.dart
index cc4530b5..e9faa510 100644
--- a/lib/src/utils/log.dart
+++ b/lib/src/utils/log.dart
@@ -35,6 +35,7 @@ class Log {
   static final _gray09 = AnsiPen()..gray(level: 0.9);
   static int _numberOfTasksCompleted = 0;
   static int _lastMessageLength = 0;
+  static Map<String, String> tasks = {};
 
   /// Log with colors.
   Log();
@@ -81,6 +82,7 @@ class Log {
 
   /// Info log on a new task
   static void startingTask(String name) {
+    tasks[name] = 'start';
     final emptyStr = _getlastMessageemptyStringLength();
     _lastMessageLength = name.length;
     _renderProgressBar();
@@ -89,9 +91,10 @@ class Log {
 
   /// Info log on a completed task
   static void taskCompleted(String name) {
+    tasks[name] = 'completed';
     _numberOfTasksCompleted++;
     stdout.writeCharCode(13);
-    stdout.write(_green('☑ '));
+    stdout.write(_green('✓ '));
     stdout.writeln(
         '$name                                                             ');
     if (_numberOfTasksCompleted >= _numberOfAllTasks) {
@@ -101,6 +104,46 @@ class Log {
     }
   }
 
+  /// Info log on a skipped task.
+  ///
+  /// e.g when some operations implicitly trigger related tasks for example,
+  /// uploading debug symbols for a Windows build may also queue a sourcemap upload
+  /// if the sourcemaps upload config is set up
+  static void taskSkipped(String name) {
+    tasks[name] = 'skipped';
+    stdout.writeCharCode(13);
+    stdout.write(_green('⏭ '));
+    stdout.writeln(
+        '$name                                                             ');
+  }
+
+  /// Logs a summary of executed tasks
+  static void tasksSummary() {
+    stdout.writeln();
+    stdout.writeln(_gray09('Tasks Summary:'));
+    var completedCount = tasks.values.where((s) => s == 'completed').length;
+    var skippedCount = tasks.values.where((s) => s == 'skipped').length;
+    var startedCount = tasks.values.where((s) => s == 'started').length;
+
+    stdout.writeln(_green('✔ Completed: $completedCount'));
+    stdout.writeln(_yellow('⏭ Skipped: $skippedCount'));
+    stdout.writeln();
+
+    tasks.forEach((name, status) {
+      if (status == 'completed' || status == 'skipped') {
+        String icon = status == 'completed' ? '✔' : '⏭';
+        AnsiPen pen = status == 'completed' ? _green : _yellow;
+        stdout.writeln(pen('$icon $name'));
+      } else if (status == 'started') {
+        // This case is very unlikely to happen but let's still log it if it does
+        AnsiPen pen = _yellow;
+        stdout
+            .writeln(pen('$startedCount tasks were started but not finished.'));
+      }
+    });
+    stdout.writeln();
+  }
+
   static String _getlastMessageemptyStringLength() {
     var emptyStr = '';
     for (var i = 0; i < _lastMessageLength + 8; i++) {