fix: Prevent appending uploadTask more than once

src/Sentry.Unity.Editor/Android/AndroidManifestConfiguration.cs

@@ -304,7 +304,7 @@ internal void SetupSymbolsUpload(string unityProjectPath, string gradleProjectPa
         {
             symbolsUpload.RemoveUploadFromGradleFile();
 
-            if (_options is { Il2CppLineNumberSupportEnabled: true })
+            if (_options is { Enabled: true, Il2CppLineNumberSupportEnabled: true })
             {
                 _logger.LogWarning("The IL2CPP line number support requires the debug symbol upload to be enabled.");
             }
@@ -327,6 +327,9 @@ internal void SetupSymbolsUpload(string unityProjectPath, string gradleProjectPa
             SentryCli.CreateSentryProperties(launcherDirectory, _sentryCliOptions!, _options!);
 
             symbolsUpload.TryCopySymbolsToGradleProject();
+            // We need to remove the old upload task first as the project persists across consecutive builds and the
+            // cli options might have changed
+            symbolsUpload.RemoveUploadFromGradleFile();
             symbolsUpload.AppendUploadToGradleFile(sentryCliPath);
         }
         catch (Exception e)

src/Sentry.Unity.Editor/Android/DebugSymbolUpload.cs

@@ -1,3 +1,4 @@
+using System;
 using System.Collections.Generic;
 using System.IO;
 using System.Text;
@@ -30,8 +31,8 @@ internal class DebugSymbolUpload
     private readonly List<string> _symbolUploadPaths;
     private readonly string _mappingFilePath;
 
-    private const string SymbolUploadTaskStartComment = "// Autogenerated Sentry symbol upload task [start]";
-    private const string SymbolUploadTaskEndComment = "// Autogenerated Sentry symbol upload task [end]";
+    internal const string SymbolUploadTaskStartComment = "// Autogenerated Sentry symbol upload task [start]";
+    internal const string SymbolUploadTaskEndComment = "// Autogenerated Sentry symbol upload task [end]";
     private const string SentryCliMarker = "SENTRY_CLI";
     private const string UploadArgsMarker = "UPLOAD_ARGS";
     private const string ProguardArgsMarker = "PROGUARD_ARGS";
@@ -102,8 +103,6 @@ public DebugSymbolUpload(IDiagnosticLogger logger,
 
     public void AppendUploadToGradleFile(string sentryCliPath)
     {
-        RemoveUploadFromGradleFile();
-
         _logger.LogInfo("Appending debug symbols upload task to gradle file.");
 
         sentryCliPath = ConvertSlashes(sentryCliPath);
@@ -162,10 +161,17 @@ public void AppendUploadToGradleFile(string sentryCliPath)
         symbolUploadText = symbolUploadText.Replace(UploadArgsMarker, uploadDifArguments);
         symbolUploadText = symbolUploadText.Replace(ProguardArgsMarker, uploadProguardArguments);
 
-        using var streamWriter = File.AppendText(_gradleScriptPath);
-        streamWriter.WriteLine(SymbolUploadTaskStartComment);
-        streamWriter.WriteLine(symbolUploadText);
-        streamWriter.WriteLine(SymbolUploadTaskEndComment);
+        var gradleBuildFile = LoadGradleScript();
+        if (gradleBuildFile.Contains("task sentryUploadSymbols"))
+        {
+            throw new InvalidOperationException("Failed to create Debug Symbol Upload Task. Task already exists in gradle file. Consider creating a clean build.");
+        }
+
+        var stringBuilder = new StringBuilder(gradleBuildFile);
+        stringBuilder.AppendLine(SymbolUploadTaskStartComment);
+        stringBuilder.AppendLine(symbolUploadText);
+        stringBuilder.AppendLine(SymbolUploadTaskEndComment);
+        File.WriteAllText(_gradleScriptPath, stringBuilder.ToString());
     }
 
     private string LoadGradleScript()
@@ -182,13 +188,14 @@ public void RemoveUploadFromGradleFile()
     {
         _logger.LogDebug("Attempting to remove the previous upload task from the gradle project.");
         var gradleBuildFile = LoadGradleScript();
-        if (!gradleBuildFile.Contains("sentry.properties"))
+        if (!gradleBuildFile.Contains(SymbolUploadTaskStartComment))
         {
             _logger.LogDebug("No previous upload task found.");
             return;
         }
 
-        var regex = new Regex(Regex.Escape(SymbolUploadTaskStartComment) + ".*" + Regex.Escape(SymbolUploadTaskEndComment), RegexOptions.Singleline);
+        var pattern = Regex.Escape(SymbolUploadTaskStartComment) + @"\r?\n.*?\r?\n" + Regex.Escape(SymbolUploadTaskEndComment);
+        var regex = new Regex(pattern, RegexOptions.Singleline);
         gradleBuildFile = regex.Replace(gradleBuildFile, "");
 
         using var streamWriter = File.CreateText(_gradleScriptPath);

test/Sentry.Unity.Editor.Tests/Android/DebugSymbolUploadTests.cs

@@ -122,6 +122,16 @@ public void AppendUploadToGradleFile_BuildGradleFileDoesNotExist_ThrowsFileNotFo
         Assert.AreEqual(GetGradleFilePath(), ex.FileName);
     }
 
+    [Test]
+    public void AppendUploadToGradleFile_TaskAlreadyExists_ThrowsInvalidOperationException()
+    {
+        var sut = _fixture.GetSut();
+        sut.AppendUploadToGradleFile(_fixture.SentryCliPath);
+
+        var ex = Assert.Throws<InvalidOperationException>(() => sut.AppendUploadToGradleFile(_fixture.SentryCliPath));
+        StringAssert.Contains("Task already exists in gradle file", ex.Message);
+    }
+
     [Test]
     [TestCase(false, false, false)]
     [TestCase(true, false, false)]
@@ -214,6 +224,29 @@ public void RemoveUploadTaskFromGradleFile_UploadHasBeenAdded_RemovesUploadTask(
         StringAssert.DoesNotContain("sentry.properties", actualFileContent);
     }
 
+    [Test]
+    public void RemoveUploadTaskFromGradleFile_MultipleConsecutiveRemovals_HandlesCorrectly()
+    {
+        var sut = _fixture.GetSut();
+
+        // Add and remove multiple times to simulate consecutive builds
+        for (var i = 0; i < 3; i++)
+        {
+            var gradleFile  = File.ReadAllText(GetGradleFilePath());
+            StringAssert.DoesNotContain("task sentryUploadSymbols", gradleFile);
+
+            sut.AppendUploadToGradleFile(_fixture.SentryCliPath);
+
+            gradleFile = File.ReadAllText(GetGradleFilePath());
+            StringAssert.Contains("task sentryUploadSymbols", gradleFile);
+
+            sut.RemoveUploadFromGradleFile();
+
+            gradleFile = File.ReadAllText(GetGradleFilePath());
+            StringAssert.DoesNotContain("task sentryUploadSymbols", gradleFile);
+        }
+    }
+
     [Test]
     [TestCase("2019.4")]
     [TestCase("2020.3")]