diff --git a/clang-tools-extra/clangd/refactor/tweaks/DefineOutline.cpp b/clang-tools-extra/clangd/refactor/tweaks/DefineOutline.cpp
--- a/clang-tools-extra/clangd/refactor/tweaks/DefineOutline.cpp
+++ b/clang-tools-extra/clangd/refactor/tweaks/DefineOutline.cpp
@@ -239,21 +239,36 @@
   DelAttr(FD->getAttr<OverrideAttr>());
   DelAttr(FD->getAttr<FinalAttr>());
 
-  if (FD->isVirtualAsWritten()) {
-    SourceRange SpecRange{FD->getBeginLoc(), FD->getLocation()};
-    bool HasErrors = true;
-
-    // Clang allows duplicating virtual specifiers so check for multiple
-    // occurances.
-    for (const auto &Tok : TokBuf.expandedTokens(SpecRange)) {
-      if (Tok.kind() != tok::kw_virtual)
+  auto DeleteKeyword = [&](tok::TokenKind Kind, SourceRange FromRange,
+                           bool AllowMultiple = false) {
+    bool FoundAny = false;
+    for (const auto &Tok : TokBuf.expandedTokens(FromRange)) {
+      if (Tok.kind() != Kind)
         continue;
+      if (FoundAny && !AllowMultiple) {
+        Errors = llvm::joinErrors(
+            std::move(Errors),
+            llvm::createStringError(
+                llvm::inconvertibleErrorCode(),
+                (llvm::StringRef("define outline: can't move outline as "
+                                 "multiple `") +
+                 tok::getKeywordSpelling(Kind) + "` keywords exist.")
+                    .str()));
+        break;
+      }
+      FoundAny = true;
       auto Spelling = TokBuf.spelledForExpanded(llvm::makeArrayRef(Tok));
       if (!Spelling) {
-        HasErrors = true;
+        Errors = llvm::joinErrors(
+            std::move(Errors),
+            llvm::createStringError(
+                llvm::inconvertibleErrorCode(),
+                (StringRef(
+                     "define outline: can't move outline as can't remove `") +
+                 tok::getKeywordSpelling(Kind) + "` keyword.")
+                    .str()));
         break;
       }
-      HasErrors = false;
       CharSourceRange DelRange =
           syntax::Token::range(SM, Spelling->front(), Spelling->back())
               .toCharRange(SM);
@@ -261,14 +276,22 @@
               DeclarationCleanups.add(tooling::Replacement(SM, DelRange, "")))
         Errors = llvm::joinErrors(std::move(Errors), std::move(Err));
     }
-    if (HasErrors) {
+    if (!FoundAny)
       Errors = llvm::joinErrors(
           std::move(Errors),
-          llvm::createStringError(llvm::inconvertibleErrorCode(),
-                                  "define outline: Can't move out of line as "
-                                  "function has a macro `virtual` specifier."));
-    }
-  }
+          llvm::createStringError(
+              llvm::inconvertibleErrorCode(),
+              (StringRef(
+                   "define outline: can't move outline as couldn't find `") +
+               tok::getKeywordSpelling(Kind) + "` keyword to remove.")
+                  .str()));
+  };
+
+  if (FD->isVirtualAsWritten())
+    DeleteKeyword(tok::kw_virtual, {FD->getBeginLoc(), FD->getLocation()},
+                  true);
+  if (isa<CXXMethodDecl>(FD) && cast<CXXMethodDecl>(FD)->isStatic())
+    DeleteKeyword(tok::kw_static, {FD->getBeginLoc(), FD->getLocation()});
 
   if (Errors)
     return std::move(Errors);
diff --git a/clang-tools-extra/clangd/unittests/TweakTests.cpp b/clang-tools-extra/clangd/unittests/TweakTests.cpp
--- a/clang-tools-extra/clangd/unittests/TweakTests.cpp
+++ b/clang-tools-extra/clangd/unittests/TweakTests.cpp
@@ -2142,6 +2142,17 @@
             };)cpp",
           "void B::foo()   {}\n",
       },
+      {
+          R"cpp(
+            struct A {
+              static void fo^o() {}
+            };)cpp",
+          R"cpp(
+            struct A {
+              static void foo() ;
+            };)cpp",
+          " void A::foo() {}\n",
+      },
   };
   for (const auto &Case : Cases) {
     SCOPED_TRACE(Case.Test);
@@ -2236,6 +2247,24 @@
             STUPID_MACRO(sizeof sizeof int) void foo() ;
           };)cpp",
        " void A::foo() {}\n"},
+      {R"cpp(#define STAT static
+          struct A {
+            STAT void f^oo() {}
+          };)cpp",
+       R"cpp(#define STAT static
+          struct A {
+            STAT void foo() ;
+          };)cpp",
+       " void A::foo() {}\n"},
+      {R"cpp(#define STUPID_MACRO(X) static
+          struct A {
+            STUPID_MACRO(sizeof sizeof int) void f^oo() {}
+          };)cpp",
+       R"cpp(#define STUPID_MACRO(X) static
+          struct A {
+            STUPID_MACRO(sizeof sizeof int) void foo() ;
+          };)cpp",
+       " void A::foo() {}\n"},
   };
   for (const auto &Case : Cases) {
     SCOPED_TRACE(Case.Test);
@@ -2360,8 +2389,8 @@
           struct A {
             VIRT fo^o() {}
           };)cpp",
-          "fail: define outline: Can't move out of line as function has a "
-          "macro `virtual` specifier."},
+          "fail: define outline: can't move outline as can't remove `virtual` "
+          "keyword."},
       {
           R"cpp(
           #define OVERFINAL final override