diff --git a/Analysis/include/Luau/Autocomplete.h b/Analysis/include/Luau/Autocomplete.h
index 5e8d6605..f40f8b49 100644
--- a/Analysis/include/Luau/Autocomplete.h
+++ b/Analysis/include/Luau/Autocomplete.h
@@ -19,6 +19,17 @@ struct TypeChecker;
 
 using ModulePtr = std::shared_ptr<Module>;
 
+enum class AutocompleteContext
+{
+    Unknown,
+    Expression,
+    Statement,
+    Property,
+    Type,
+    Keyword,
+    String,
+};
+
 enum class AutocompleteEntryKind
 {
     Property,
@@ -66,11 +77,13 @@ struct AutocompleteResult
 {
     AutocompleteEntryMap entryMap;
     std::vector<AstNode*> ancestry;
+    AutocompleteContext context = AutocompleteContext::Unknown;
 
     AutocompleteResult() = default;
-    AutocompleteResult(AutocompleteEntryMap entryMap, std::vector<AstNode*> ancestry)
+    AutocompleteResult(AutocompleteEntryMap entryMap, std::vector<AstNode*> ancestry, AutocompleteContext context)
         : entryMap(std::move(entryMap))
         , ancestry(std::move(ancestry))
+        , context(context)
     {
     }
 };
diff --git a/Analysis/src/Autocomplete.cpp b/Analysis/src/Autocomplete.cpp
index a57a789f..8d5cc723 100644
--- a/Analysis/src/Autocomplete.cpp
+++ b/Analysis/src/Autocomplete.cpp
@@ -1200,7 +1200,7 @@ static bool autocompleteIfElseExpression(
     }
 }
 
-static void autocompleteExpression(const SourceModule& sourceModule, const Module& module, const TypeChecker& typeChecker, TypeArena* typeArena,
+static AutocompleteContext autocompleteExpression(const SourceModule& sourceModule, const Module& module, const TypeChecker& typeChecker, TypeArena* typeArena,
     const std::vector<AstNode*>& ancestry, Position position, AutocompleteEntryMap& result)
 {
     LUAU_ASSERT(!ancestry.empty());
@@ -1213,9 +1213,9 @@ static void autocompleteExpression(const SourceModule& sourceModule, const Modul
             autocompleteProps(module, typeArena, *it, PropIndexType::Point, ancestry, result);
     }
     else if (autocompleteIfElseExpression(node, ancestry, position, result))
-        return;
+        return AutocompleteContext::Keyword;
     else if (node->is<AstExprFunction>())
-        return;
+        return AutocompleteContext::Unknown;
     else
     {
         // This is inefficient. :(
@@ -1260,14 +1260,16 @@ static void autocompleteExpression(const SourceModule& sourceModule, const Modul
         if (auto ty = findExpectedTypeAt(module, node, position))
             autocompleteStringSingleton(*ty, true, result);
     }
+
+    return AutocompleteContext::Expression;
 }
 
-static AutocompleteEntryMap autocompleteExpression(const SourceModule& sourceModule, const Module& module, const TypeChecker& typeChecker,
+static AutocompleteResult autocompleteExpression(const SourceModule& sourceModule, const Module& module, const TypeChecker& typeChecker,
     TypeArena* typeArena, const std::vector<AstNode*>& ancestry, Position position)
 {
     AutocompleteEntryMap result;
-    autocompleteExpression(sourceModule, module, typeChecker, typeArena, ancestry, position, result);
-    return result;
+    AutocompleteContext context = autocompleteExpression(sourceModule, module, typeChecker, typeArena, ancestry, position, result);
+    return {result, ancestry, context};
 }
 
 static std::optional<const ClassTypeVar*> getMethodContainingClass(const ModulePtr& module, AstExpr* funcExpr)
@@ -1406,27 +1408,27 @@ static AutocompleteResult autocomplete(const SourceModule& sourceModule, const M
 
         if (!FFlag::LuauSelfCallAutocompleteFix3 && isString(ty))
             return {
-                autocompleteProps(*module, typeArena, typeChecker.globalScope->bindings[AstName{"string"}].typeId, indexType, ancestry), ancestry};
+                autocompleteProps(*module, typeArena, typeChecker.globalScope->bindings[AstName{"string"}].typeId, indexType, ancestry), ancestry, AutocompleteContext::Property};
         else
-            return {autocompleteProps(*module, typeArena, ty, indexType, ancestry), ancestry};
+            return {autocompleteProps(*module, typeArena, ty, indexType, ancestry), ancestry, AutocompleteContext::Property};
     }
     else if (auto typeReference = node->as<AstTypeReference>())
     {
         if (typeReference->prefix)
-            return {autocompleteModuleTypes(*module, position, typeReference->prefix->value), ancestry};
+            return {autocompleteModuleTypes(*module, position, typeReference->prefix->value), ancestry, AutocompleteContext::Type};
         else
-            return {autocompleteTypeNames(*module, position, ancestry), ancestry};
+            return {autocompleteTypeNames(*module, position, ancestry), ancestry, AutocompleteContext::Type};
     }
     else if (node->is<AstTypeError>())
     {
-        return {autocompleteTypeNames(*module, position, ancestry), ancestry};
+        return {autocompleteTypeNames(*module, position, ancestry), ancestry, AutocompleteContext::Type};
     }
     else if (AstStatLocal* statLocal = node->as<AstStatLocal>())
     {
         if (statLocal->vars.size == 1 && (!statLocal->equalsSignLocation || position < statLocal->equalsSignLocation->begin))
-            return {{{"function", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+            return {{{"function", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Unknown};
         else if (statLocal->equalsSignLocation && position >= statLocal->equalsSignLocation->end)
-            return {autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position), ancestry};
+            return autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position);
         else
             return {};
     }
@@ -1436,16 +1438,16 @@ static AutocompleteResult autocomplete(const SourceModule& sourceModule, const M
         if (!statFor->hasDo || position < statFor->doLocation.begin)
         {
             if (!statFor->from->is<AstExprError>() && !statFor->to->is<AstExprError>() && (!statFor->step || !statFor->step->is<AstExprError>()))
-                return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+                return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Keyword};
 
             if (statFor->from->location.containsClosed(position) || statFor->to->location.containsClosed(position) ||
                 (statFor->step && statFor->step->location.containsClosed(position)))
-                return {autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position), ancestry};
+                return autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position);
 
             return {};
         }
 
-        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry};
+        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry, AutocompleteContext::Statement};
     }
 
     else if (AstStatForIn* statForIn = parent->as<AstStatForIn>(); statForIn && (node->is<AstStatBlock>() || isIdentifier(node)))
@@ -1461,7 +1463,7 @@ static AutocompleteResult autocomplete(const SourceModule& sourceModule, const M
                 return {};
             }
 
-            return {{{"in", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+            return {{{"in", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Keyword};
         }
 
         if (!statForIn->hasDo || position <= statForIn->doLocation.begin)
@@ -1470,10 +1472,10 @@ static AutocompleteResult autocomplete(const SourceModule& sourceModule, const M
             AstExpr* lastExpr = statForIn->values.data[statForIn->values.size - 1];
 
             if (lastExpr->location.containsClosed(position))
-                return {autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position), ancestry};
+                return autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position);
 
             if (position > lastExpr->location.end)
-                return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+                return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Keyword};
 
             return {}; // Not sure what this means
         }
@@ -1483,45 +1485,45 @@ static AutocompleteResult autocomplete(const SourceModule& sourceModule, const M
         // The AST looks a bit differently if the cursor is at a position where only the "do" keyword is allowed.
         // ex "for f in f do"
         if (!statForIn->hasDo)
-            return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+            return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Keyword};
 
-        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry};
+        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry, AutocompleteContext::Statement};
     }
 
     else if (AstStatWhile* statWhile = parent->as<AstStatWhile>(); node->is<AstStatBlock>() && statWhile)
     {
         if (!statWhile->hasDo && !statWhile->condition->is<AstStatError>() && position > statWhile->condition->location.end)
-            return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+            return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Keyword};
 
         if (!statWhile->hasDo || position < statWhile->doLocation.begin)
-            return {autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position), ancestry};
+            return autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position);
 
         if (statWhile->hasDo && position > statWhile->doLocation.end)
-            return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry};
+            return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry, AutocompleteContext::Statement};
     }
 
     else if (AstStatWhile* statWhile = extractStat<AstStatWhile>(ancestry); statWhile && !statWhile->hasDo)
-        return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+        return {{{"do", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Keyword};
 
     else if (AstStatIf* statIf = node->as<AstStatIf>(); statIf && !statIf->elseLocation.has_value())
     {
         return {
-            {{"else", AutocompleteEntry{AutocompleteEntryKind::Keyword}}, {"elseif", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+            {{"else", AutocompleteEntry{AutocompleteEntryKind::Keyword}}, {"elseif", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Keyword};
     }
     else if (AstStatIf* statIf = parent->as<AstStatIf>(); statIf && node->is<AstStatBlock>())
     {
         if (statIf->condition->is<AstExprError>())
-            return {autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position), ancestry};
+            return autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position);
         else if (!statIf->thenLocation || statIf->thenLocation->containsClosed(position))
-            return {{{"then", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+            return {{{"then", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Keyword};
     }
     else if (AstStatIf* statIf = extractStat<AstStatIf>(ancestry);
              statIf && (!statIf->thenLocation || statIf->thenLocation->containsClosed(position)))
-        return {{{"then", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry};
+        return {{{"then", AutocompleteEntry{AutocompleteEntryKind::Keyword}}}, ancestry, AutocompleteContext::Keyword};
     else if (AstStatRepeat* statRepeat = node->as<AstStatRepeat>(); statRepeat && statRepeat->condition->is<AstExprError>())
-        return {autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position), ancestry};
+        return autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position);
     else if (AstStatRepeat* statRepeat = extractStat<AstStatRepeat>(ancestry); statRepeat)
-        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry};
+        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry, AutocompleteContext::Statement};
     else if (AstExprTable* exprTable = parent->as<AstExprTable>(); exprTable && (node->is<AstExprGlobal>() || node->is<AstExprConstantString>()))
     {
         for (const auto& [kind, key, value] : exprTable->items)
@@ -1547,7 +1549,7 @@ static AutocompleteResult autocomplete(const SourceModule& sourceModule, const M
                     if (!key)
                         autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position, result);
 
-                    return {result, ancestry};
+                    return {result, ancestry, AutocompleteContext::Property};
                 }
 
                 break;
@@ -1555,11 +1557,11 @@ static AutocompleteResult autocomplete(const SourceModule& sourceModule, const M
         }
     }
     else if (isIdentifier(node) && (parent->is<AstStatExpr>() || parent->is<AstStatError>()))
-        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry};
+        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry, AutocompleteContext::Statement};
 
     if (std::optional<AutocompleteEntryMap> ret = autocompleteStringParams(sourceModule, module, ancestry, position, callback))
     {
-        return {*ret, ancestry};
+        return {*ret, ancestry, AutocompleteContext::String};
     }
     else if (node->is<AstExprConstantString>())
     {
@@ -1585,7 +1587,7 @@ static AutocompleteResult autocomplete(const SourceModule& sourceModule, const M
             }
         }
 
-        return {result, ancestry};
+        return {result, ancestry, AutocompleteContext::String};
     }
 
     if (node->is<AstExprConstantNumber>())
@@ -1594,9 +1596,9 @@ static AutocompleteResult autocomplete(const SourceModule& sourceModule, const M
     }
 
     if (node->asExpr())
-        return {autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position), ancestry};
+        return autocompleteExpression(sourceModule, *module, typeChecker, typeArena, ancestry, position);
     else if (node->asStat())
-        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry};
+        return {autocompleteStatement(sourceModule, *module, ancestry, position), ancestry, AutocompleteContext::Statement};
 
     return {};
 }
diff --git a/docs/_pages/lint.md b/docs/_pages/lint.md
index 340d35a2..fd3c595c 100644
--- a/docs/_pages/lint.md
+++ b/docs/_pages/lint.md
@@ -327,3 +327,26 @@ Luau uses comments that start from `!` to control certain aspects of analysis, f
 -- Unknown comment directive 'nostrict'; did you mean 'nonstrict'?"
 ```
 ```
+
+## IntegerParsing (27)
+
+Luau parses hexadecimal and binary literals as 64-bit integers before converting them to Luau numbers. As a result, numbers that exceed 2^64 are silently truncated to 2^64, which can result in unexpected program behavior. This warning flags literals that are truncated:
+
+```
+-- Hexadecimal number literal exceeded available precision and has been truncated to 2^64
+local x = 0x1111111111111111111111111111111111111
+```
+
+## ComparisonPrecedence (28)
+
+Because of operator precedence rules, not X == Y parses as (not X) == Y; however, often the intent was to invert the result of the comparison. This warning flags erroneous conditions like that, as well as flagging cases where two comparisons happen in a row without any parentheses:
+
+```
+-- not X == Y is equivalent to (not X) == Y; consider using X ~= Y, or wrap one of the expressions in parentheses to silence
+if not x == 5 then
+end
+
+-- X <= Y <= Z is equivalent to (X <= Y) <= Z; wrap one of the expressions in parentheses to silence
+if 1 <= x <= 3 then
+end
+```
diff --git a/tests/Autocomplete.test.cpp b/tests/Autocomplete.test.cpp
index 75c5a606..0f17531b 100644
--- a/tests/Autocomplete.test.cpp
+++ b/tests/Autocomplete.test.cpp
@@ -129,6 +129,7 @@ TEST_CASE_FIXTURE(ACFixture, "empty_program")
     CHECK(!ac.entryMap.empty());
     CHECK(ac.entryMap.count("table"));
     CHECK(ac.entryMap.count("math"));
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "local_initializer")
@@ -138,6 +139,7 @@ TEST_CASE_FIXTURE(ACFixture, "local_initializer")
     auto ac = autocomplete('1');
     CHECK(ac.entryMap.count("table"));
     CHECK(ac.entryMap.count("math"));
+    CHECK_EQ(ac.context, AutocompleteContext::Expression);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "leave_numbers_alone")
@@ -146,6 +148,7 @@ TEST_CASE_FIXTURE(ACFixture, "leave_numbers_alone")
 
     auto ac = autocomplete('1');
     CHECK(ac.entryMap.empty());
+    CHECK_EQ(ac.context, AutocompleteContext::Unknown);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "user_defined_globals")
@@ -157,6 +160,7 @@ TEST_CASE_FIXTURE(ACFixture, "user_defined_globals")
     CHECK(ac.entryMap.count("myLocal"));
     CHECK(ac.entryMap.count("table"));
     CHECK(ac.entryMap.count("math"));
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "dont_suggest_local_before_its_definition")
@@ -191,6 +195,7 @@ TEST_CASE_FIXTURE(ACFixture, "recursive_function")
 
     auto ac = autocomplete('1');
     CHECK(ac.entryMap.count("foo"));
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "nested_recursive_function")
@@ -293,6 +298,7 @@ TEST_CASE_FIXTURE(ACBuiltinsFixture, "get_member_completions")
     CHECK(ac.entryMap.count("find"));
     CHECK(ac.entryMap.count("pack"));
     CHECK(!ac.entryMap.count("math"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "nested_member_completions")
@@ -306,6 +312,7 @@ TEST_CASE_FIXTURE(ACFixture, "nested_member_completions")
     CHECK_EQ(2, ac.entryMap.size());
     CHECK(ac.entryMap.count("def"));
     CHECK(ac.entryMap.count("egh"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "unsealed_table")
@@ -319,6 +326,7 @@ TEST_CASE_FIXTURE(ACFixture, "unsealed_table")
     auto ac = autocomplete('1');
     CHECK_EQ(1, ac.entryMap.size());
     CHECK(ac.entryMap.count("prop"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "unsealed_table_2")
@@ -333,6 +341,7 @@ TEST_CASE_FIXTURE(ACFixture, "unsealed_table_2")
     auto ac = autocomplete('1');
     CHECK_EQ(1, ac.entryMap.size());
     CHECK(ac.entryMap.count("prop"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "cyclic_table")
@@ -346,6 +355,7 @@ TEST_CASE_FIXTURE(ACFixture, "cyclic_table")
 
     auto ac = autocomplete('1');
     CHECK(ac.entryMap.count("abc"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "table_union")
@@ -361,6 +371,7 @@ TEST_CASE_FIXTURE(ACFixture, "table_union")
     auto ac = autocomplete('1');
     CHECK_EQ(1, ac.entryMap.size());
     CHECK(ac.entryMap.count("b2"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "table_intersection")
@@ -378,6 +389,7 @@ TEST_CASE_FIXTURE(ACFixture, "table_intersection")
     CHECK(ac.entryMap.count("a1"));
     CHECK(ac.entryMap.count("b2"));
     CHECK(ac.entryMap.count("c3"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACBuiltinsFixture, "get_string_completions")
@@ -389,6 +401,7 @@ TEST_CASE_FIXTURE(ACBuiltinsFixture, "get_string_completions")
     auto ac = autocomplete('1');
 
     CHECK_EQ(17, ac.entryMap.size());
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "get_suggestions_for_new_statement")
@@ -400,6 +413,7 @@ TEST_CASE_FIXTURE(ACFixture, "get_suggestions_for_new_statement")
     CHECK_NE(0, ac.entryMap.size());
 
     CHECK(ac.entryMap.count("table"));
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "get_suggestions_for_the_very_start_of_the_script")
@@ -412,6 +426,7 @@ TEST_CASE_FIXTURE(ACFixture, "get_suggestions_for_the_very_start_of_the_script")
     auto ac = autocomplete('1');
 
     CHECK(ac.entryMap.count("table"));
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "method_call_inside_function_body")
@@ -429,6 +444,7 @@ TEST_CASE_FIXTURE(ACFixture, "method_call_inside_function_body")
     CHECK_NE(0, ac.entryMap.size());
 
     CHECK(!ac.entryMap.count("math"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACBuiltinsFixture, "method_call_inside_if_conditional")
@@ -442,6 +458,7 @@ TEST_CASE_FIXTURE(ACBuiltinsFixture, "method_call_inside_if_conditional")
     CHECK_NE(0, ac.entryMap.size());
     CHECK(ac.entryMap.count("concat"));
     CHECK(!ac.entryMap.count("math"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "statement_between_two_statements")
@@ -459,6 +476,8 @@ TEST_CASE_FIXTURE(ACFixture, "statement_between_two_statements")
     CHECK_NE(0, ac.entryMap.size());
 
     CHECK(ac.entryMap.count("getmyscripts"));
+
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "bias_toward_inner_scope")
@@ -476,6 +495,7 @@ TEST_CASE_FIXTURE(ACFixture, "bias_toward_inner_scope")
     auto ac = autocomplete('1');
 
     CHECK(ac.entryMap.count("A"));
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 
     TypeId t = follow(*ac.entryMap["A"].type);
     const TableTypeVar* tt = get<TableTypeVar>(t);
@@ -489,10 +509,12 @@ TEST_CASE_FIXTURE(ACFixture, "recommend_statement_starting_keywords")
     check("@1");
     auto ac = autocomplete('1');
     CHECK(ac.entryMap.count("local"));
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 
     check("local i = @1");
     auto ac2 = autocomplete('1');
     CHECK(!ac2.entryMap.count("local"));
+    CHECK_EQ(ac2.context, AutocompleteContext::Expression);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "do_not_overwrite_context_sensitive_kws")
@@ -508,6 +530,7 @@ TEST_CASE_FIXTURE(ACFixture, "do_not_overwrite_context_sensitive_kws")
 
     AutocompleteEntry entry = ac.entryMap["continue"];
     CHECK(entry.kind == AutocompleteEntryKind::Binding);
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "dont_offer_any_suggestions_from_within_a_comment")
@@ -525,6 +548,7 @@ TEST_CASE_FIXTURE(ACFixture, "dont_offer_any_suggestions_from_within_a_comment")
     auto ac = autocomplete('1');
 
     CHECK_EQ(0, ac.entryMap.size());
+    CHECK_EQ(ac.context, AutocompleteContext::Unknown);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "dont_offer_any_suggestions_from_the_end_of_a_comment")
@@ -536,6 +560,7 @@ TEST_CASE_FIXTURE(ACFixture, "dont_offer_any_suggestions_from_the_end_of_a_comme
     auto ac = autocomplete('1');
 
     CHECK_EQ(0, ac.entryMap.size());
+    CHECK_EQ(ac.context, AutocompleteContext::Unknown);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "dont_offer_any_suggestions_from_within_a_broken_comment")
@@ -547,6 +572,7 @@ TEST_CASE_FIXTURE(ACFixture, "dont_offer_any_suggestions_from_within_a_broken_co
     auto ac = autocomplete('1');
 
     CHECK_EQ(0, ac.entryMap.size());
+    CHECK_EQ(ac.context, AutocompleteContext::Unknown);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "dont_offer_any_suggestions_from_within_a_broken_comment_at_the_very_end_of_the_file")
@@ -555,6 +581,7 @@ TEST_CASE_FIXTURE(ACFixture, "dont_offer_any_suggestions_from_within_a_broken_co
 
     auto ac = autocomplete('1');
     CHECK_EQ(0, ac.entryMap.size());
+    CHECK_EQ(ac.context, AutocompleteContext::Unknown);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_middle_keywords")
@@ -566,6 +593,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_middle_keywords")
     auto ac1 = autocomplete('1');
     CHECK_EQ(ac1.entryMap.count("do"), 0);
     CHECK_EQ(ac1.entryMap.count("end"), 0);
+    CHECK_EQ(ac1.context, AutocompleteContext::Unknown);
 
     check(R"(
         for x =@1 1
@@ -574,6 +602,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_middle_keywords")
     auto ac2 = autocomplete('1');
     CHECK_EQ(ac2.entryMap.count("do"), 0);
     CHECK_EQ(ac2.entryMap.count("end"), 0);
+    CHECK_EQ(ac2.context, AutocompleteContext::Unknown);
 
     check(R"(
         for x = 1,@1 2
@@ -582,6 +611,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_middle_keywords")
     auto ac3 = autocomplete('1');
     CHECK_EQ(1, ac3.entryMap.size());
     CHECK_EQ(ac3.entryMap.count("do"), 1);
+    CHECK_EQ(ac3.context, AutocompleteContext::Keyword);
 
     check(R"(
         for x = 1, @12,
@@ -590,6 +620,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_middle_keywords")
     auto ac4 = autocomplete('1');
     CHECK_EQ(ac4.entryMap.count("do"), 0);
     CHECK_EQ(ac4.entryMap.count("end"), 0);
+    CHECK_EQ(ac4.context, AutocompleteContext::Expression);
 
     check(R"(
         for x = 1, 2, @15
@@ -598,6 +629,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_middle_keywords")
     auto ac5 = autocomplete('1');
     CHECK_EQ(ac5.entryMap.count("do"), 1);
     CHECK_EQ(ac5.entryMap.count("end"), 0);
+    CHECK_EQ(ac5.context, AutocompleteContext::Keyword);
 
     check(R"(
         for x = 1, 2, 5 f@1
@@ -606,6 +638,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_middle_keywords")
     auto ac6 = autocomplete('1');
     CHECK_EQ(ac6.entryMap.size(), 1);
     CHECK_EQ(ac6.entryMap.count("do"), 1);
+    CHECK_EQ(ac6.context, AutocompleteContext::Keyword);
 
     check(R"(
         for x = 1, 2, 5 do      @1
@@ -613,6 +646,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_middle_keywords")
 
     auto ac7 = autocomplete('1');
     CHECK_EQ(ac7.entryMap.count("end"), 1);
+    CHECK_EQ(ac7.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_in_middle_keywords")
@@ -623,6 +657,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_in_middle_keywords")
 
     auto ac1 = autocomplete('1');
     CHECK_EQ(0, ac1.entryMap.size());
+    CHECK_EQ(ac1.context, AutocompleteContext::Unknown);
 
     check(R"(
         for x@1 @2
@@ -630,10 +665,12 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_in_middle_keywords")
 
     auto ac2 = autocomplete('1');
     CHECK_EQ(0, ac2.entryMap.size());
+    CHECK_EQ(ac2.context, AutocompleteContext::Unknown);
 
     auto ac2a = autocomplete('2');
     CHECK_EQ(1, ac2a.entryMap.size());
     CHECK_EQ(1, ac2a.entryMap.count("in"));
+    CHECK_EQ(ac2a.context, AutocompleteContext::Keyword);
 
     check(R"(
         for x in y@1
@@ -642,6 +679,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_in_middle_keywords")
     auto ac3 = autocomplete('1');
     CHECK_EQ(ac3.entryMap.count("table"), 1);
     CHECK_EQ(ac3.entryMap.count("do"), 0);
+    CHECK_EQ(ac3.context, AutocompleteContext::Expression);
 
     check(R"(
         for x in y @1
@@ -650,6 +688,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_in_middle_keywords")
     auto ac4 = autocomplete('1');
     CHECK_EQ(ac4.entryMap.size(), 1);
     CHECK_EQ(ac4.entryMap.count("do"), 1);
+    CHECK_EQ(ac4.context, AutocompleteContext::Keyword);
 
     check(R"(
         for x in f f@1
@@ -658,6 +697,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_in_middle_keywords")
     auto ac5 = autocomplete('1');
     CHECK_EQ(ac5.entryMap.size(), 1);
     CHECK_EQ(ac5.entryMap.count("do"), 1);
+    CHECK_EQ(ac5.context, AutocompleteContext::Keyword);
 
     check(R"(
         for x in y do  @1
@@ -668,6 +708,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_in_middle_keywords")
     CHECK_EQ(ac6.entryMap.count("table"), 1);
     CHECK_EQ(ac6.entryMap.count("end"), 1);
     CHECK_EQ(ac6.entryMap.count("function"), 1);
+    CHECK_EQ(ac6.context, AutocompleteContext::Statement);
 
     check(R"(
         for x in y do e@1
@@ -678,6 +719,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_for_in_middle_keywords")
     CHECK_EQ(ac7.entryMap.count("table"), 1);
     CHECK_EQ(ac7.entryMap.count("end"), 1);
     CHECK_EQ(ac7.entryMap.count("function"), 1);
+    CHECK_EQ(ac7.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_while_middle_keywords")
@@ -689,6 +731,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_while_middle_keywords")
     auto ac1 = autocomplete('1');
     CHECK_EQ(ac1.entryMap.count("do"), 0);
     CHECK_EQ(ac1.entryMap.count("end"), 0);
+    CHECK_EQ(ac1.context, AutocompleteContext::Expression);
 
     check(R"(
         while true @1
@@ -697,6 +740,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_while_middle_keywords")
     auto ac2 = autocomplete('1');
     CHECK_EQ(1, ac2.entryMap.size());
     CHECK_EQ(ac2.entryMap.count("do"), 1);
+    CHECK_EQ(ac2.context, AutocompleteContext::Keyword);
 
     check(R"(
         while true do  @1
@@ -704,6 +748,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_while_middle_keywords")
 
     auto ac3 = autocomplete('1');
     CHECK_EQ(ac3.entryMap.count("end"), 1);
+    CHECK_EQ(ac3.context, AutocompleteContext::Statement);
 
     check(R"(
         while true d@1
@@ -712,6 +757,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_while_middle_keywords")
     auto ac4 = autocomplete('1');
     CHECK_EQ(1, ac4.entryMap.size());
     CHECK_EQ(ac4.entryMap.count("do"), 1);
+    CHECK_EQ(ac4.context, AutocompleteContext::Keyword);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_if_middle_keywords")
@@ -728,6 +774,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_if_middle_keywords")
     CHECK_EQ(ac1.entryMap.count("else"), 0);
     CHECK_EQ(ac1.entryMap.count("elseif"), 0);
     CHECK_EQ(ac1.entryMap.count("end"), 0);
+    CHECK_EQ(ac1.context, AutocompleteContext::Expression);
 
     check(R"(
         if x  @1
@@ -739,6 +786,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_if_middle_keywords")
     CHECK_EQ(ac2.entryMap.count("else"), 0);
     CHECK_EQ(ac2.entryMap.count("elseif"), 0);
     CHECK_EQ(ac2.entryMap.count("end"), 0);
+    CHECK_EQ(ac2.context, AutocompleteContext::Keyword);
 
     check(R"(
         if x t@1
@@ -747,6 +795,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_if_middle_keywords")
     auto ac3 = autocomplete('1');
     CHECK_EQ(1, ac3.entryMap.size());
     CHECK_EQ(ac3.entryMap.count("then"), 1);
+    CHECK_EQ(ac3.context, AutocompleteContext::Keyword);
 
     check(R"(
         if x then
@@ -760,6 +809,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_if_middle_keywords")
     CHECK_EQ(ac4.entryMap.count("function"), 1);
     CHECK_EQ(ac4.entryMap.count("elseif"), 1);
     CHECK_EQ(ac4.entryMap.count("end"), 0);
+    CHECK_EQ(ac4.context, AutocompleteContext::Statement);
 
     check(R"(
         if x then
@@ -772,6 +822,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_if_middle_keywords")
     CHECK_EQ(ac4a.entryMap.count("table"), 1);
     CHECK_EQ(ac4a.entryMap.count("else"), 1);
     CHECK_EQ(ac4a.entryMap.count("elseif"), 1);
+    CHECK_EQ(ac4a.context, AutocompleteContext::Statement);
 
     check(R"(
         if x then
@@ -786,6 +837,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_if_middle_keywords")
     CHECK_EQ(ac5.entryMap.count("else"), 0);
     CHECK_EQ(ac5.entryMap.count("elseif"), 0);
     CHECK_EQ(ac5.entryMap.count("end"), 0);
+    CHECK_EQ(ac5.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_until_in_repeat")
@@ -797,6 +849,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_until_in_repeat")
     auto ac = autocomplete('1');
     CHECK_EQ(ac.entryMap.count("table"), 1);
     CHECK_EQ(ac.entryMap.count("until"), 1);
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_until_expression")
@@ -808,6 +861,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_until_expression")
 
     auto ac = autocomplete('1');
     CHECK_EQ(ac.entryMap.count("table"), 1);
+    CHECK_EQ(ac.context, AutocompleteContext::Expression);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "local_names")
@@ -819,6 +873,7 @@ TEST_CASE_FIXTURE(ACFixture, "local_names")
     auto ac1 = autocomplete('1');
     CHECK_EQ(ac1.entryMap.size(), 1);
     CHECK_EQ(ac1.entryMap.count("function"), 1);
+    CHECK_EQ(ac1.context, AutocompleteContext::Unknown);
 
     check(R"(
         local ab, cd@1
@@ -826,6 +881,7 @@ TEST_CASE_FIXTURE(ACFixture, "local_names")
 
     auto ac2 = autocomplete('1');
     CHECK(ac2.entryMap.empty());
+    CHECK_EQ(ac2.context, AutocompleteContext::Unknown);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_end_with_fn_exprs")
@@ -836,6 +892,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_end_with_fn_exprs")
 
     auto ac = autocomplete('1');
     CHECK_EQ(ac.entryMap.count("end"), 1);
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_end_with_lambda")
@@ -846,6 +903,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_end_with_lambda")
 
     auto ac = autocomplete('1');
     CHECK_EQ(ac.entryMap.count("end"), 1);
+    CHECK_EQ(ac.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "stop_at_first_stat_when_recommending_keywords")
@@ -858,6 +916,7 @@ TEST_CASE_FIXTURE(ACFixture, "stop_at_first_stat_when_recommending_keywords")
     auto ac1 = autocomplete('1');
     CHECK_EQ(ac1.entryMap.count("in"), 1);
     CHECK_EQ(ac1.entryMap.count("until"), 0);
+    CHECK_EQ(ac1.context, AutocompleteContext::Keyword);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_repeat_middle_keyword")
@@ -980,6 +1039,7 @@ TEST_CASE_FIXTURE(ACFixture, "local_function_params")
     auto ac2 = autocomplete('1');
     CHECK_EQ(ac2.entryMap.count("abc"), 1);
     CHECK_EQ(ac2.entryMap.count("def"), 1);
+    CHECK_EQ(ac2.context, AutocompleteContext::Statement);
 
     check(R"(
         local function abc(def, ghi@1)
@@ -988,6 +1048,7 @@ TEST_CASE_FIXTURE(ACFixture, "local_function_params")
 
     auto ac3 = autocomplete('1');
     CHECK(ac3.entryMap.empty());
+    CHECK_EQ(ac3.context, AutocompleteContext::Unknown);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "global_function_params")
@@ -1022,6 +1083,7 @@ TEST_CASE_FIXTURE(ACFixture, "global_function_params")
     auto ac2 = autocomplete('1');
     CHECK_EQ(ac2.entryMap.count("abc"), 1);
     CHECK_EQ(ac2.entryMap.count("def"), 1);
+    CHECK_EQ(ac2.context, AutocompleteContext::Statement);
 
     check(R"(
         function abc(def, ghi@1)
@@ -1030,6 +1092,7 @@ TEST_CASE_FIXTURE(ACFixture, "global_function_params")
 
     auto ac3 = autocomplete('1');
     CHECK(ac3.entryMap.empty());
+    CHECK_EQ(ac3.context, AutocompleteContext::Unknown);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "arguments_to_global_lambda")
@@ -1074,6 +1137,7 @@ TEST_CASE_FIXTURE(ACFixture, "function_expr_params")
 
     auto ac2 = autocomplete('1');
     CHECK_EQ(ac2.entryMap.count("def"), 1);
+    CHECK_EQ(ac2.context, AutocompleteContext::Statement);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "local_initializer")
@@ -1135,6 +1199,7 @@ local b: string = "don't trip"
 
     CHECK(ac.entryMap.count("nil"));
     CHECK(ac.entryMap.count("number"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "private_types")
@@ -1203,6 +1268,7 @@ local a: aa
     auto ac = Luau::autocomplete(frontend, "Module/B", Position{2, 11}, nullCallback);
 
     CHECK(ac.entryMap.count("aaa"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "module_type_members")
@@ -1227,6 +1293,7 @@ local a: aaa.
     CHECK_EQ(2, ac.entryMap.size());
     CHECK(ac.entryMap.count("A"));
     CHECK(ac.entryMap.count("B"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "argument_types")
@@ -1240,6 +1307,7 @@ local b: string = "don't trip"
 
     CHECK(ac.entryMap.count("nil"));
     CHECK(ac.entryMap.count("number"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "return_types")
@@ -1253,6 +1321,7 @@ local b: string = "don't trip"
 
     CHECK(ac.entryMap.count("nil"));
     CHECK(ac.entryMap.count("number"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "as_types")
@@ -1266,6 +1335,7 @@ local b: number = (a :: n@1
 
     CHECK(ac.entryMap.count("nil"));
     CHECK(ac.entryMap.count("number"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "function_type_types")
@@ -1314,6 +1384,7 @@ local b: string = "don't trip"
     auto ac = autocomplete('1');
 
     CHECK(ac.entryMap.count("Tee"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "type_correct_suggestion_in_argument")
@@ -1402,6 +1473,7 @@ local b: Foo = { a = a.@1
     CHECK(ac.entryMap.count("one"));
     CHECK(ac.entryMap["one"].typeCorrect == TypeCorrectKind::Correct);
     CHECK(ac.entryMap["two"].typeCorrect == TypeCorrectKind::None);
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     check(R"(
 type Foo = { a: number, b: string }
@@ -1414,6 +1486,7 @@ local b: Foo = { b = a.@1
     CHECK(ac.entryMap.count("two"));
     CHECK(ac.entryMap["two"].typeCorrect == TypeCorrectKind::Correct);
     CHECK(ac.entryMap["one"].typeCorrect == TypeCorrectKind::None);
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "type_correct_function_return_types")
@@ -2395,6 +2468,7 @@ local t: Test = { f@1 }
     auto ac = autocomplete('1');
     CHECK(ac.entryMap.count("first"));
     CHECK(ac.entryMap.count("second"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     // Intersection
     check(R"(
@@ -2405,6 +2479,7 @@ local t: Test = { f@1 }
     ac = autocomplete('1');
     CHECK(ac.entryMap.count("first"));
     CHECK(ac.entryMap.count("second"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     // Union
     check(R"(
@@ -2416,6 +2491,7 @@ local t: Test = { s@1 }
     CHECK(ac.entryMap.count("second"));
     CHECK(!ac.entryMap.count("first"));
     CHECK(!ac.entryMap.count("third"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     // No parenthesis suggestion
     check(R"(
@@ -2426,6 +2502,7 @@ local t: Test = { f@1 }
     ac = autocomplete('1');
     CHECK(ac.entryMap.count("first"));
     CHECK(ac.entryMap["first"].parens == ParenthesesRecommendation::None);
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     // When key is changed
     check(R"(
@@ -2436,6 +2513,7 @@ local t: Test = { f@1 = 2 }
     ac = autocomplete('1');
     CHECK(ac.entryMap.count("first"));
     CHECK(ac.entryMap.count("second"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     // Alternative key syntax
     check(R"(
@@ -2446,6 +2524,7 @@ local t: Test = { ["f@1"] }
     ac = autocomplete('1');
     CHECK(ac.entryMap.count("first"));
     CHECK(ac.entryMap.count("second"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     // Not an alternative key syntax
     check(R"(
@@ -2456,6 +2535,7 @@ local t: Test = { "f@1" }
     ac = autocomplete('1');
     CHECK(!ac.entryMap.count("first"));
     CHECK(!ac.entryMap.count("second"));
+    CHECK_EQ(ac.context, AutocompleteContext::String);
 
     // Skip keys that are already defined
     check(R"(
@@ -2466,6 +2546,7 @@ local t: Test = { first = 2, s@1 }
     ac = autocomplete('1');
     CHECK(!ac.entryMap.count("first"));
     CHECK(ac.entryMap.count("second"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     // Don't skip active key
     check(R"(
@@ -2476,6 +2557,7 @@ local t: Test = { first@1 }
     ac = autocomplete('1');
     CHECK(ac.entryMap.count("first"));
     CHECK(ac.entryMap.count("second"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     // Inference after first key
     check(R"(
@@ -2488,6 +2570,7 @@ local t = {
     ac = autocomplete('1');
     CHECK(ac.entryMap.count("first"));
     CHECK(ac.entryMap.count("second"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 
     check(R"(
 local t = {
@@ -2499,6 +2582,7 @@ local t = {
     ac = autocomplete('1');
     CHECK(ac.entryMap.count("first"));
     CHECK(ac.entryMap.count("second"));
+    CHECK_EQ(ac.context, AutocompleteContext::Property);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_documentation_symbols")
@@ -2542,6 +2626,7 @@ a = if temp then even elseif true then temp else e@9
     CHECK(ac.entryMap.count("then") == 0);
     CHECK(ac.entryMap.count("else") == 0);
     CHECK(ac.entryMap.count("elseif") == 0);
+    CHECK_EQ(ac.context, AutocompleteContext::Expression);
 
     ac = autocomplete('2');
     CHECK(ac.entryMap.count("temp") == 0);
@@ -2549,18 +2634,21 @@ a = if temp then even elseif true then temp else e@9
     CHECK(ac.entryMap.count("then"));
     CHECK(ac.entryMap.count("else") == 0);
     CHECK(ac.entryMap.count("elseif") == 0);
+    CHECK_EQ(ac.context, AutocompleteContext::Keyword);
 
     ac = autocomplete('3');
     CHECK(ac.entryMap.count("even"));
     CHECK(ac.entryMap.count("then") == 0);
     CHECK(ac.entryMap.count("else") == 0);
     CHECK(ac.entryMap.count("elseif") == 0);
+    CHECK_EQ(ac.context, AutocompleteContext::Expression);
 
     ac = autocomplete('4');
     CHECK(ac.entryMap.count("even") == 0);
     CHECK(ac.entryMap.count("then") == 0);
     CHECK(ac.entryMap.count("else"));
     CHECK(ac.entryMap.count("elseif"));
+    CHECK_EQ(ac.context, AutocompleteContext::Keyword);
 
     ac = autocomplete('5');
     CHECK(ac.entryMap.count("temp"));
@@ -2568,6 +2656,7 @@ a = if temp then even elseif true then temp else e@9
     CHECK(ac.entryMap.count("then") == 0);
     CHECK(ac.entryMap.count("else") == 0);
     CHECK(ac.entryMap.count("elseif") == 0);
+    CHECK_EQ(ac.context, AutocompleteContext::Expression);
 
     ac = autocomplete('6');
     CHECK(ac.entryMap.count("temp") == 0);
@@ -2575,6 +2664,7 @@ a = if temp then even elseif true then temp else e@9
     CHECK(ac.entryMap.count("then"));
     CHECK(ac.entryMap.count("else") == 0);
     CHECK(ac.entryMap.count("elseif") == 0);
+    CHECK_EQ(ac.context, AutocompleteContext::Keyword);
 
     ac = autocomplete('7');
     CHECK(ac.entryMap.count("temp"));
@@ -2582,17 +2672,20 @@ a = if temp then even elseif true then temp else e@9
     CHECK(ac.entryMap.count("then") == 0);
     CHECK(ac.entryMap.count("else") == 0);
     CHECK(ac.entryMap.count("elseif") == 0);
+    CHECK_EQ(ac.context, AutocompleteContext::Expression);
 
     ac = autocomplete('8');
     CHECK(ac.entryMap.count("even") == 0);
     CHECK(ac.entryMap.count("then") == 0);
     CHECK(ac.entryMap.count("else"));
     CHECK(ac.entryMap.count("elseif"));
+    CHECK_EQ(ac.context, AutocompleteContext::Keyword);
 
     ac = autocomplete('9');
     CHECK(ac.entryMap.count("then") == 0);
     CHECK(ac.entryMap.count("else") == 0);
     CHECK(ac.entryMap.count("elseif") == 0);
+    CHECK_EQ(ac.context, AutocompleteContext::Expression);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_if_else_regression")
@@ -2626,6 +2719,7 @@ local a: A<(number, s@1>
 
     CHECK(ac.entryMap.count("number"));
     CHECK(ac.entryMap.count("string"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_first_function_arg_expected_type")
@@ -2686,6 +2780,7 @@ type A<T = @1> = () -> T
 
     CHECK(ac.entryMap.count("number"));
     CHECK(ac.entryMap.count("string"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_default_type_pack_parameters")
@@ -2698,6 +2793,7 @@ type A<T... = ...@1> = () -> T
 
     CHECK(ac.entryMap.count("number"));
     CHECK(ac.entryMap.count("string"));
+    CHECK_EQ(ac.context, AutocompleteContext::Type);
 }
 
 TEST_CASE_FIXTURE(ACBuiltinsFixture, "autocomplete_oop_implicit_self")
@@ -2752,16 +2848,19 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_string_singletons")
 
     CHECK(ac.entryMap.count("cat"));
     CHECK(ac.entryMap.count("dog"));
+    CHECK_EQ(ac.context, AutocompleteContext::String);
 
     ac = autocomplete('2');
 
     CHECK(ac.entryMap.count("\"cat\""));
     CHECK(ac.entryMap.count("\"dog\""));
+    CHECK_EQ(ac.context, AutocompleteContext::Expression);
 
     ac = autocomplete('3');
 
     CHECK(ac.entryMap.count("cat"));
     CHECK(ac.entryMap.count("dog"));
+    CHECK_EQ(ac.context, AutocompleteContext::String);
 
     check(R"(
         type tagged = {tag:"cat", fieldx:number} | {tag:"dog", fieldy:number}
@@ -2772,6 +2871,7 @@ TEST_CASE_FIXTURE(ACFixture, "autocomplete_string_singletons")
 
     CHECK(ac.entryMap.count("cat"));
     CHECK(ac.entryMap.count("dog"));
+    CHECK_EQ(ac.context, AutocompleteContext::String);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_string_singleton_equality")
@@ -2808,6 +2908,7 @@ f(@1)
     CHECK(ac.entryMap["true"].typeCorrect == TypeCorrectKind::Correct);
     REQUIRE(ac.entryMap.count("false"));
     CHECK(ac.entryMap["false"].typeCorrect == TypeCorrectKind::None);
+    CHECK_EQ(ac.context, AutocompleteContext::Expression);
 }
 
 TEST_CASE_FIXTURE(ACFixture, "autocomplete_string_singleton_escape")