diff --git a/documentation_files/builtindocumentation.py b/documentation_files/builtindocumentation.py
--- a/documentation_files/builtindocumentation.py
+++ b/documentation_files/builtindocumentation.py
@@ -152,6 +152,7 @@
     def writelines(self,sequence): return None
     def __iter__(self): return self
     def __next__(self): return ""
+    def __enter__(self): return self
     buffer = _io_TextIOWrapper() # Not quite
     closed = True
     encoding = ""
diff --git a/duchain/declarationbuilder.cpp b/duchain/declarationbuilder.cpp
--- a/duchain/declarationbuilder.cpp
+++ b/duchain/declarationbuilder.cpp
@@ -364,7 +364,20 @@
         // For statements like "with open(f) as x", a new variable must be created; do this here.
         ExpressionVisitor v(currentContext());
         v.visitNode(node->contextExpression);
-        visitVariableDeclaration<Declaration>(node->optionalVars, nullptr, v.lastType());
+        auto mgrType = v.lastType();
+        auto enterType = mgrType; // If we can't find __enter__(), assume it returns `self` like file objects.
+
+        static const IndexedIdentifier enterId(KDevelop::Identifier("__enter__"));
+
+        DUChainReadLocker lock;
+        if ( auto enterFunc = dynamic_cast<FunctionDeclaration*>(
+                Helper::accessAttribute(mgrType, enterId, topContext())
+                                                                )) {
+            enterType = enterFunc->type<FunctionType>()->returnType();
+        }
+        lock.unlock();
+        // This may be any assignable expression, e.g. `with foo() as bar[3]: ...`
+        assignToUnknown(node->optionalVars, enterType);
     }
     Python::AstDefaultVisitor::visitWithItem(node);
 }
diff --git a/parser/ast.h b/parser/ast.h
--- a/parser/ast.h
+++ b/parser/ast.h
@@ -368,7 +368,7 @@
 public:
     WithItemAst(Ast* parent);
     ExpressionAst* contextExpression;
-    NameAst* optionalVars;
+    ExpressionAst* optionalVars;
 };
 
 class KDEVPYTHONPARSER_EXPORT WithAst : public StatementAst {
diff --git a/parser/generated.h b/parser/generated.h
--- a/parser/generated.h
+++ b/parser/generated.h
@@ -780,7 +780,7 @@
         if ( ! node ) return nullptr;
                 WithItemAst* v = new  WithItemAst(parent());
             nodeStack.push(v); v->contextExpression = static_cast<ExpressionAst*>(visitNode(node->context_expr)); nodeStack.pop();
-            nodeStack.push(v); v->optionalVars = static_cast<NameAst*>(visitNode(node->optional_vars)); nodeStack.pop();
+            nodeStack.push(v); v->optionalVars = static_cast<ExpressionAst*>(visitNode(node->optional_vars)); nodeStack.pop();
         return v;
     }
 
diff --git a/parser/python36.sdef b/parser/python36.sdef
--- a/parser/python36.sdef
+++ b/parser/python36.sdef
@@ -99,4 +99,4 @@
 RULE_FOR _arg;KIND any;ACTIONS create|ArgAst set|argumentName~>arg set|annotation->ExpressionAst,annotation;;
 RULE_FOR _keyword;KIND any;ACTIONS create|KeywordAst set|argumentName~>arg set|value->ExpressionAst,value;;
 RULE_FOR _alias;KIND any;ACTIONS create|AliasAst set|name~>name set|asName~>asname;;
-RULE_FOR _withitem;KIND any; ACTIONS create|WithItemAst set|contextExpression->ExpressionAst,context_expr set|optionalVars->NameAst,optional_vars;;
+RULE_FOR _withitem;KIND any; ACTIONS create|WithItemAst set|contextExpression->ExpressionAst,context_expr set|optionalVars->ExpressionAst,optional_vars;;