diff --git a/metals/src/main/scala/scala/meta/internal/metals/Compilers.scala b/metals/src/main/scala/scala/meta/internal/metals/Compilers.scala
index 14cdce0e069..a418039138f 100644
--- a/metals/src/main/scala/scala/meta/internal/metals/Compilers.scala
+++ b/metals/src/main/scala/scala/meta/internal/metals/Compilers.scala
@@ -112,6 +112,8 @@ class Compilers(
     )
 
   private val worksheetsDigests = new TrieMap[AbsolutePath, String]()
+  private val wasSuccessfullyCompiled =
+    new TrieMap[BuildTargetIdentifier, Boolean]()
 
   private val cache = jcache.asScala
   private def buildTargetPCFromCache(
@@ -272,6 +274,11 @@ class Compilers(
     val isSuccessful = report.getErrors == 0
     buildTargetPCFromCache(report.getTarget).foreach(_.restart(isSuccessful))
 
+    wasSuccessfullyCompiled.updateWith(report.getTarget()) {
+      case Some(true) => Some(true)
+      case _ => Some(isSuccessful)
+    }
+
     if (isSuccessful) {
       // Restart PC for all build targets that depend on this target since the classfiles
       // may have changed.
@@ -1188,7 +1195,7 @@ class Compilers(
       classpath: Seq[Path],
       search: SymbolSearch,
   ): PresentationCompiler = {
-    newCompiler(
+    val pc = newCompiler(
       mtags,
       target.scalac.getOptions().asScala.toSeq,
       classpath,
@@ -1196,6 +1203,11 @@ class Compilers(
       target.scalac.getTarget.getUri,
     ).withBuildTargetName(target.displayName)
       .withCompilerFiles(new TargetCompilerFiles(target.id))
+
+    wasSuccessfullyCompiled
+      .get(target.scalac.getTarget())
+      .map(pc.withWasSuccessfullyCompiled)
+      .getOrElse(pc)
   }
 
   def newCompiler(
diff --git a/mtags-interfaces/src/main/java/scala/meta/pc/PresentationCompiler.java b/mtags-interfaces/src/main/java/scala/meta/pc/PresentationCompiler.java
index 800d3d2f7dd..ad3cdf3209d 100644
--- a/mtags-interfaces/src/main/java/scala/meta/pc/PresentationCompiler.java
+++ b/mtags-interfaces/src/main/java/scala/meta/pc/PresentationCompiler.java
@@ -206,7 +206,7 @@ public CompletableFuture<List<SyntheticDecoration>> syntheticDecorations(Synthet
 	/**
 	 * Clean the symbol table and other mutable state in the compiler.
 	 */
-	public void restart(Boolean successfulCompilation) {
+	public void restart(boolean successfulCompilation) {
 		restart();
 	}
 
@@ -324,4 +324,8 @@ public abstract PresentationCompiler newInstance(String buildTargetIdentifier, L
 	 */
 	public abstract String scalaVersion();
 
+	public PresentationCompiler withWasSuccessfullyCompiled(boolean wasSuccessful) { 
+		return this;
+	}
+
 }
diff --git a/mtags-shared/src/main/scala/scala/meta/internal/pc/CompilerWrapper.scala b/mtags-shared/src/main/scala/scala/meta/internal/pc/CompilerWrapper.scala
index a6932b9d02e..8836721b802 100644
--- a/mtags-shared/src/main/scala/scala/meta/internal/pc/CompilerWrapper.scala
+++ b/mtags-shared/src/main/scala/scala/meta/internal/pc/CompilerWrapper.scala
@@ -28,5 +28,5 @@ case class OutlineFiles(
 )
 
 object OutlineFiles {
-  def empty = OutlineFiles(Nil)
+  def empty: OutlineFiles = OutlineFiles(Nil)
 }
diff --git a/mtags/src/main/scala-2.11/scala/meta/internal/pc/Compat.scala b/mtags/src/main/scala-2.11/scala/meta/internal/pc/Compat.scala
index 3d2936e86f8..8b77efec49d 100644
--- a/mtags/src/main/scala-2.11/scala/meta/internal/pc/Compat.scala
+++ b/mtags/src/main/scala-2.11/scala/meta/internal/pc/Compat.scala
@@ -2,7 +2,6 @@ package scala.meta.internal.pc
 
 import scala.tools.nsc.reporters.Reporter
 import scala.tools.nsc.reporters.StoreReporter
-import scala.meta.pc.VirtualFileParams
 
 trait Compat { this: MetalsGlobal =>
   def metalsFunctionArgTypes(tpe: Type): List[Type] = {
@@ -21,7 +20,7 @@ trait Compat { this: MetalsGlobal =>
 
   def constantType(c: ConstantType): ConstantType = c
 
-  def runOutline(files: List[VirtualFileParams]): Unit = {
+  def runOutline(files: OutlineFiles): Unit = {
     // no outline compilation for 2.11
   }
 }
diff --git a/mtags/src/main/scala-2.12/scala/meta/internal/pc/Compat.scala b/mtags/src/main/scala-2.12/scala/meta/internal/pc/Compat.scala
index 772066b055f..cc1c8c51a6f 100644
--- a/mtags/src/main/scala-2.12/scala/meta/internal/pc/Compat.scala
+++ b/mtags/src/main/scala-2.12/scala/meta/internal/pc/Compat.scala
@@ -2,6 +2,7 @@ package scala.meta.internal.pc
 
 import scala.tools.nsc.reporters.Reporter
 import scala.tools.nsc.reporters.StoreReporter
+
 import scala.meta.pc.VirtualFileParams
 
 trait Compat { this: MetalsGlobal =>
@@ -18,18 +19,32 @@ trait Compat { this: MetalsGlobal =>
 
   def constantType(c: ConstantType): ConstantType = c
 
-  def runOutline(files: List[VirtualFileParams]): Unit = {
+  def runOutline(files: OutlineFiles): Unit = {
     this.settings.Youtline.value = true
+    runOutline(files.files)
+    if (files.firstCompileSubstitute) {
+      // if first compilation substitute we compile all files twice
+      // first to emit symbols, second so signatures have information about those symbols
+      // this isn't a perfect strategy but much better than single compile
+      runOutline(files.files, forceNewUnit = true)
+    }
+    this.settings.Youtline.value = false
+  }
+
+  private def runOutline(
+      files: List[VirtualFileParams],
+      forceNewUnit: Boolean = false
+  ): Unit = {
     files.foreach { params =>
       val unit = this.addCompilationUnit(
         params.text(),
         params.uri.toString(),
         cursor = None,
-        isOutline = true
+        isOutline = true,
+        forceNew = forceNewUnit
       )
       this.typeCheck(unit)
       this.richCompilationCache.put(params.uri().toString(), unit)
     }
-    this.settings.Youtline.value = false
   }
 }
diff --git a/mtags/src/main/scala-2.13/scala/meta/internal/pc/Compat.scala b/mtags/src/main/scala-2.13/scala/meta/internal/pc/Compat.scala
index eea56572e90..19e8ec15b9c 100644
--- a/mtags/src/main/scala-2.13/scala/meta/internal/pc/Compat.scala
+++ b/mtags/src/main/scala-2.13/scala/meta/internal/pc/Compat.scala
@@ -27,27 +27,31 @@ trait Compat { this: MetalsGlobal =>
     if (c.value.isSuitableLiteralType) LiteralType(c.value) else c
 
   def runOutline(files: OutlineFiles): Unit = {
+    this.settings.Youtline.value = true
     runOutline(files.files)
-    if(files.firstCompileSubstitute) {
+    if (files.firstCompileSubstitute) {
       // if first compilation substitute we compile all files twice
       // first to emit symbols, second so signatures have information about those symbols
       // this isn't a perfect strategy but much better than single compile
       runOutline(files.files, forceNewUnit = true)
     }
+    this.settings.Youtline.value = false
   }
 
-  private def runOutline(files: List[VirtualFileParams], forceNewUnit: Boolean = false): Unit = {
-    this.settings.Youtline.value = true
+  private def runOutline(
+      files: List[VirtualFileParams],
+      forceNewUnit: Boolean = false
+  ): Unit = {
     files.foreach { params =>
       val unit = this.addCompilationUnit(
         params.text(),
         params.uri.toString(),
         cursor = None,
-        isOutline = true
+        isOutline = true,
+        forceNew = forceNewUnit
       )
       this.typeCheck(unit)
       this.richCompilationCache.put(params.uri().toString(), unit)
     }
-    this.settings.Youtline.value = false
   }
 }
diff --git a/mtags/src/main/scala-2/scala/meta/internal/pc/MetalsGlobal.scala b/mtags/src/main/scala-2/scala/meta/internal/pc/MetalsGlobal.scala
index c7eaef5319c..4bc0c4cfef5 100644
--- a/mtags/src/main/scala-2/scala/meta/internal/pc/MetalsGlobal.scala
+++ b/mtags/src/main/scala-2/scala/meta/internal/pc/MetalsGlobal.scala
@@ -66,7 +66,8 @@ class MetalsGlobal(
 
   val logger: Logger = Logger.getLogger(classOf[MetalsGlobal].getName)
 
-  val richCompilationCache: TrieMap[String,RichCompilationUnit] = TrieMap.empty[String, RichCompilationUnit]
+  val richCompilationCache: TrieMap[String, RichCompilationUnit] =
+    TrieMap.empty[String, RichCompilationUnit]
 
   // for those paths units were
   val fullyCompiled: mutable.Set[String] = mutable.Set.empty[String]
@@ -652,7 +653,8 @@ class MetalsGlobal(
       filename: String,
       cursor: Option[Int],
       cursorName: String = CURSOR,
-      isOutline: Boolean = false
+      isOutline: Boolean = false,
+      forceNew: Boolean = false
   ): RichCompilationUnit = {
     val codeWithCursor = cursor match {
       case Some(offset) =>
@@ -671,11 +673,11 @@ class MetalsGlobal(
           if util.Arrays.equals(
             value.source.content,
             richUnit.source.content
-          ) && (isOutline || fullyCompiled(filename)) =>
+          ) && (isOutline || fullyCompiled(filename)) && !forceNew =>
         value
       case _ =>
         unitOfFile(richUnit.source.file) = richUnit
-        if(!isOutline) {
+        if (!isOutline) {
           fullyCompiled += filename
         } else {
           fullyCompiled -= filename
diff --git a/mtags/src/main/scala-2/scala/meta/internal/pc/ScalaCompilerAccess.scala b/mtags/src/main/scala-2/scala/meta/internal/pc/ScalaCompilerAccess.scala
index af9681f0054..3ad5ab0d4b7 100644
--- a/mtags/src/main/scala-2/scala/meta/internal/pc/ScalaCompilerAccess.scala
+++ b/mtags/src/main/scala-2/scala/meta/internal/pc/ScalaCompilerAccess.scala
@@ -9,7 +9,6 @@ import scala.util.control.NonFatal
 
 import scala.meta.internal.metals.ReportContext
 import scala.meta.pc.PresentationCompilerConfig
-import scala.meta.pc.VirtualFileParams
 
 class ScalaCompilerWrapper(global: MetalsGlobal)
     extends CompilerWrapper[StoreReporter, MetalsGlobal] {
diff --git a/mtags/src/main/scala-2/scala/meta/internal/pc/ScalaPresentationCompiler.scala b/mtags/src/main/scala-2/scala/meta/internal/pc/ScalaPresentationCompiler.scala
index 5ac337be247..69556f1a128 100644
--- a/mtags/src/main/scala-2/scala/meta/internal/pc/ScalaPresentationCompiler.scala
+++ b/mtags/src/main/scala-2/scala/meta/internal/pc/ScalaPresentationCompiler.scala
@@ -67,10 +67,14 @@ case class ScalaPresentationCompiler(
     config: PresentationCompilerConfig = PresentationCompilerConfigImpl(),
     folderPath: Option[Path] = None,
     reportsLevel: ReportLevel = ReportLevel.Info,
-    compilerFiles: Option[CompilerFiles] = None
+    compilerFiles: Option[CompilerFiles] = None,
+    wasSuccessfullyCompiledInitial: Option[Boolean] = None
 ) extends PresentationCompiler {
 
-  private val wasFirstCompilationSuccessful = new util.concurrent.atomic.AtomicReference[Option[Boolean]](None)
+  private val wasSuccessfullyCompiled =
+    new util.concurrent.atomic.AtomicReference[Option[Boolean]](
+      wasSuccessfullyCompiledInitial
+    )
 
   implicit val executionContext: ExecutionContextExecutor = ec
 
@@ -147,13 +151,14 @@ case class ScalaPresentationCompiler(
 
   def restart(): Unit = restoreOutlineAndRestart()
 
-  override def restart(wasSuccessful: java.lang.Boolean): Unit = {
-    wasFirstCompilationSuccessful.updateAndGet {
+  override def restart(wasSuccessful: Boolean): Unit = {
+    wasSuccessfullyCompiled.updateAndGet {
       case None => Some(wasSuccessful)
+      case _ if wasSuccessful => Some(true)
       case value => value
     }
 
-    if(wasSuccessful) {
+    if (wasSuccessful) {
       changedDocuments.clear()
       compilerAccess.shutdownCurrentCompiler()
     } else {
@@ -168,26 +173,25 @@ case class ScalaPresentationCompiler(
         EmptyCancelToken
       ) { pc =>
         /* we will still want outline recompiled if the compilation was not succesful */
-        pc.compiler().richCompilationCache.foreach {
-          case (uriString, unit) =>
-            try {
-              val text = unit.source.content.mkString
-              val uri = uriString.toAbsolutePath.toURI
-              val params =
-                CompilerOffsetParams(uri, text, 0, EmptyCancelToken)
-              changedDocuments += uri -> params
-            } catch {
-              case NonFatal(error) =>
-                reportContex.incognito.create(
-                  Report(
-                    "restoring_cache",
-                    "Error while restoring outline compiler cache",
-                    error
-                  )
+        pc.compiler().richCompilationCache.foreach { case (uriString, unit) =>
+          try {
+            val text = unit.source.content.mkString
+            val uri = uriString.toAbsolutePath.toURI
+            val params =
+              CompilerOffsetParams(uri, text, 0, EmptyCancelToken)
+            changedDocuments += uri -> params
+          } catch {
+            case NonFatal(error) =>
+              reportContex.incognito.create(
+                Report(
+                  "restoring_cache",
+                  "Error while restoring outline compiler cache",
+                  error
                 )
-                logger
-                  .log(util.logging.Level.SEVERE, error.getMessage(), error)
-            }
+              )
+              logger
+                .log(util.logging.Level.SEVERE, error.getMessage(), error)
+          }
         }
       }
       .get()
@@ -212,8 +216,15 @@ case class ScalaPresentationCompiler(
   private def outlineFiles(
       current: VirtualFileParams
   ): OutlineFiles = {
+    val shouldCompileAll = wasSuccessfullyCompiled
+      .getAndUpdate {
+        case Some(false) => Some(true)
+        case value => value
+      }
+      .exists(!_)
+
     val result =
-      if (wasFirstCompilationSuccessful.getAndSet(Some(true)).exists(!_)) {
+      if (shouldCompileAll) {
         // if first compilation was unsuccessful we want to outline all files
         compilerFiles.iterator.flatMap(_.allPaths().asScala).foreach { path =>
           val uri = path.toUri()
@@ -222,9 +233,13 @@ case class ScalaPresentationCompiler(
             changedDocuments += uri -> CompilerOffsetParams(uri, text, 0)
           }
         }
-        OutlineFiles(changedDocuments.values.toList, firstCompileSubstitute = true)
+        OutlineFiles(
+          changedDocuments.values.toList,
+          firstCompileSubstitute = true
+        )
       } else {
-        val files = changedDocuments.values.filterNot(_.uri() == current.uri()).toList
+        val files =
+          changedDocuments.values.filterNot(_.uri() == current.uri()).toList
         OutlineFiles(files)
       }
 
@@ -282,7 +297,7 @@ case class ScalaPresentationCompiler(
 
   override def complete(
       params: OffsetParams
-  ): CompletableFuture[CompletionList] =
+  ): CompletableFuture[CompletionList] = {
     compilerAccess.withInterruptableCompiler(Some(params))(
       EmptyCompletionList(),
       params.token
@@ -290,6 +305,7 @@ case class ScalaPresentationCompiler(
       new CompletionProvider(pc.compiler(outlineFiles(params)), params)
         .completions()
     }
+  }
 
   override def implementAbstractMembers(
       params: OffsetParams
@@ -579,4 +595,11 @@ case class ScalaPresentationCompiler(
       .toList
       .asJava
   }
+
+  override def withWasSuccessfullyCompiled(
+      wasSuccessful: Boolean
+  ): PresentationCompiler = {
+    this.copy(wasSuccessfullyCompiledInitial = Some(wasSuccessful))
+  }
+
 }
diff --git a/mtags/src/main/scala-2/scala/meta/internal/pc/WorkspaceSymbolSearch.scala b/mtags/src/main/scala-2/scala/meta/internal/pc/WorkspaceSymbolSearch.scala
index 124db2b71f6..66ff4565d74 100644
--- a/mtags/src/main/scala-2/scala/meta/internal/pc/WorkspaceSymbolSearch.scala
+++ b/mtags/src/main/scala-2/scala/meta/internal/pc/WorkspaceSymbolSearch.scala
@@ -26,7 +26,7 @@ trait WorkspaceSymbolSearch { compiler: MetalsGlobal =>
             def matches = if (sym.isType)
               CompletionFuzzy.matchesSubCharacters(query, sym.name.toString())
             else CompletionFuzzy.matches(query, sym.name.toString())
-            if (sym.exists && matches) {
+            if (sym != null && sym.exists && matches) {
               try {
                 visitMember(sym)
               } catch {
diff --git a/tests/unit/src/test/scala/tests/SemanticTokensLspSuite.scala b/tests/unit/src/test/scala/tests/SemanticTokensLspSuite.scala
index 6ec2131e181..4a67f1b84d1 100644
--- a/tests/unit/src/test/scala/tests/SemanticTokensLspSuite.scala
+++ b/tests/unit/src/test/scala/tests/SemanticTokensLspSuite.scala
@@ -266,13 +266,13 @@ class SemanticTokensLspSuite extends BaseLspSuite("SemanticTokens") {
     for {
       _ <- initialize(
         s"""/metals.json
-            |{"a":{}}
-            |/a/src/main/scala/a/Main.scala
-            |
-            |/a/src/main/scala/a/OtherFile.scala
-            |package a
-            |object A
-            |""".stripMargin,
+           |{"a":{}}
+           |/a/src/main/scala/a/Main.scala
+           |
+           |/a/src/main/scala/a/OtherFile.scala
+           |package a
+           |object A
+           |""".stripMargin,
         expectError = true,
       )
       _ <- server.didChangeConfiguration(