diff --git a/clang/lib/Parse/ParseDeclCXX.cpp b/clang/lib/Parse/ParseDeclCXX.cpp
--- a/clang/lib/Parse/ParseDeclCXX.cpp
+++ b/clang/lib/Parse/ParseDeclCXX.cpp
@@ -856,6 +856,16 @@
                                        DeclFromDeclSpec);
 }
 
+static FixItHint getStaticAssertNoMessageFixIt(const Expr *AssertExpr,
+                                               SourceLocation EndExprLoc) {
+  if (const auto *BO = llvm::dyn_cast_or_null<BinaryOperator>(AssertExpr)) {
+    if (BO->getOpcode() == BO_LAnd &&
+        llvm::isa<StringLiteral>(BO->getRHS()->IgnoreImpCasts()))
+      return FixItHint::CreateReplacement(BO->getOperatorLoc(), ",");
+  }
+  return FixItHint::CreateInsertion(EndExprLoc, ", \"\"");
+}
+
 /// ParseStaticAssertDeclaration - Parse C++0x or C11 static_assert-declaration.
 ///
 /// [C++0x] static_assert-declaration:
@@ -892,12 +902,11 @@
 
   ExprResult AssertMessage;
   if (Tok.is(tok::r_paren)) {
-    Diag(Tok, getLangOpts().CPlusPlus17
-                  ? diag::warn_cxx14_compat_static_assert_no_message
-                  : diag::ext_static_assert_no_message)
-      << (getLangOpts().CPlusPlus17
-              ? FixItHint()
-              : FixItHint::CreateInsertion(Tok.getLocation(), ", \"\""));
+    if (getLangOpts().CPlusPlus17)
+      Diag(Tok, diag::warn_cxx14_compat_static_assert_no_message);
+    else
+      Diag(Tok, diag::ext_static_assert_no_message)
+          << getStaticAssertNoMessageFixIt(AssertExpr.get(), Tok.getLocation());
   } else {
     if (ExpectAndConsume(tok::comma)) {
       SkipUntil(tok::semi);
diff --git a/clang/test/FixIt/fixit-static-assert.cpp b/clang/test/FixIt/fixit-static-assert.cpp
new file mode 100644
--- /dev/null
+++ b/clang/test/FixIt/fixit-static-assert.cpp
@@ -0,0 +1,27 @@
+// RUN: %clang_cc1 -std=c++14 %s -fdiagnostics-parseable-fixits %s 2>&1 | FileCheck %s
+// Ensure no warnings are emitted in c++17.
+// RUN: %clang_cc1 -std=c++17 %s -Werror -fsyntax-only
+// RUN: %clang_cc1 -std=c++14 %s -fixit-recompile -fixit-to-temporary -Werror
+
+static_assert(true && "String");
+// CHECK-DAG: {[[@LINE-1]]:20-[[@LINE-1]]:22}:","
+
+// String literal prefixes are good.
+static_assert(true && R"(RawString)");
+// CHECK-DAG: {[[@LINE-1]]:20-[[@LINE-1]]:22}:","
+static_assert(true && L"RawString");
+// CHECK-DAG: {[[@LINE-1]]:20-[[@LINE-1]]:22}:","
+
+
+static_assert(true);
+// CHECK-DAG: {[[@LINE-1]]:19-[[@LINE-1]]:19}:", \"\""
+
+// While its technically possible to transform this to
+// static_assert(true, "String") we don't attempt this fix.
+static_assert("String" && true);
+// CHECK-DAG: {[[@LINE-1]]:31-[[@LINE-1]]:31}:", \"\""
+
+// Don't be smart and look in parentheses.
+static_assert((true && "String"));
+// CHECK-DAG: {[[@LINE-1]]:33-[[@LINE-1]]:33}:", \"\""
+