diff --git a/toolchain/lex/lex.cpp b/toolchain/lex/lex.cpp
index 025d7a5b6dff..59a9dca084dc 100644
--- a/toolchain/lex/lex.cpp
+++ b/toolchain/lex/lex.cpp
@@ -1631,8 +1631,11 @@ class Lexer::ErrorRecoveryBuffer {
       for (; old_tokens_it->first < next_offset; ++old_tokens_it) {
         buffer_->token_infos_.Add(old_tokens_it->second);
       }
-      buffer_->AddToken(info);
-      buffer_->recovery_tokens_.set(next_offset.index);
+      // Flag the token just added at its index in the merged list, which
+      // shifts past `next_offset` (the pre-insertion index) once any earlier
+      // insertion has been applied.
+      TokenIndex added = buffer_->AddToken(info);
+      buffer_->recovery_tokens_.set(added.index);
     }
     for (; old_tokens_it != old_tokens_range.end(); ++old_tokens_it) {
       buffer_->token_infos_.Add(old_tokens_it->second);
diff --git a/toolchain/lex/tokenized_buffer_test.cpp b/toolchain/lex/tokenized_buffer_test.cpp
index 051031959865..c2d389edad33 100644
--- a/toolchain/lex/tokenized_buffer_test.cpp
+++ b/toolchain/lex/tokenized_buffer_test.cpp
@@ -618,6 +618,44 @@ TEST_F(LexerTest, MismatchedGroups) {
           {.kind = TokenKind::FileEnd},
       }));
 
+  // Two recovery tokens inserted at the same point: each must be flagged at
+  // its own merged index, not the pre-insertion index of the token it was
+  // inserted before.
+  auto& buffer3b = compile_helper_.GetTokenizedBuffer("{((}");
+  EXPECT_TRUE(buffer3b.has_errors());
+  EXPECT_THAT(
+      buffer3b,
+      HasTokens(llvm::ArrayRef<ExpectedToken>{
+          {.kind = TokenKind::FileStart},
+          {.kind = TokenKind::OpenCurlyBrace, .column = 1},
+          {.kind = TokenKind::OpenParen, .column = 2},
+          {.kind = TokenKind::OpenParen, .column = 3},
+          {.kind = TokenKind::CloseParen, .column = 4, .recovery = true},
+          {.kind = TokenKind::CloseParen, .column = 4, .recovery = true},
+          {.kind = TokenKind::CloseCurlyBrace, .column = 4},
+          {.kind = TokenKind::FileEnd},
+      }));
+
+  // Recovery insertions at two separate points: the second one's merged index
+  // is shifted by the first, and a real token must not be flagged in its
+  // place.
+  auto& buffer3c = compile_helper_.GetTokenizedBuffer("{(} {(}");
+  EXPECT_TRUE(buffer3c.has_errors());
+  EXPECT_THAT(
+      buffer3c,
+      HasTokens(llvm::ArrayRef<ExpectedToken>{
+          {.kind = TokenKind::FileStart},
+          {.kind = TokenKind::OpenCurlyBrace, .column = 1},
+          {.kind = TokenKind::OpenParen, .column = 2},
+          {.kind = TokenKind::CloseParen, .column = 3, .recovery = true},
+          {.kind = TokenKind::CloseCurlyBrace, .column = 3},
+          {.kind = TokenKind::OpenCurlyBrace, .column = 5},
+          {.kind = TokenKind::OpenParen, .column = 6},
+          {.kind = TokenKind::CloseParen, .column = 7, .recovery = true},
+          {.kind = TokenKind::CloseCurlyBrace, .column = 7},
+          {.kind = TokenKind::FileEnd},
+      }));
+
   auto& buffer4 = compile_helper_.GetTokenizedBuffer(")({)");
   EXPECT_TRUE(buffer4.has_errors());
   EXPECT_THAT(