diff --git a/clang-tools-extra/clangd/CodeComplete.cpp b/clang-tools-extra/clangd/CodeComplete.cpp
--- a/clang-tools-extra/clangd/CodeComplete.cpp
+++ b/clang-tools-extra/clangd/CodeComplete.cpp
@@ -1123,7 +1123,11 @@
   // skip all includes in this case; these completions are really simple.
   PreambleBounds PreambleRegion =
       ComputePreambleBounds(*CI->getLangOpts(), *ContentsBuffer, 0);
-  bool CompletingInPreamble = PreambleRegion.Size > Input.Offset;
+  // If preamble doesn't end on a new line, include the following byte in
+  // preamble to enable include completion on a new file. e.g: #include "^
+  bool CompletingInPreamble =
+      PreambleRegion.Size + !PreambleRegion.PreambleEndsAtStartOfLine >
+      Input.Offset;
   if (Input.Patch)
     Input.Patch->apply(*CI);
   // NOTE: we must call BeginSourceFile after prepareCompilerInstance. Otherwise
diff --git a/clang-tools-extra/clangd/unittests/CodeCompleteTests.cpp b/clang-tools-extra/clangd/unittests/CodeCompleteTests.cpp
--- a/clang-tools-extra/clangd/unittests/CodeCompleteTests.cpp
+++ b/clang-tools-extra/clangd/unittests/CodeCompleteTests.cpp
@@ -2573,7 +2573,7 @@
 }
 
 TEST(CompletionTest, IncludedCompletionKinds) {
-  Annotations Test(R"cpp(#include "^")cpp");
+  Annotations Test(R"cpp(#include "^)cpp");
   auto TU = TestTU::withCode(Test.code());
   TU.AdditionalFiles["sub/bar.h"] = "";
   TU.ExtraArgs.push_back("-I" + testPath("sub"));