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 +364,21 @@
         // 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()))) {
+            if ( auto enterFuncType = enterFunc->type<FunctionType>() ) {
+                enterType = enterFuncType->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/duchain/tests/pyduchaintest.cpp b/duchain/tests/pyduchaintest.cpp
--- a/duchain/tests/pyduchaintest.cpp
+++ b/duchain/tests/pyduchaintest.cpp
@@ -871,7 +871,25 @@
                                             "        return x\n"
                                             "f = Foo()\n"
                                             "checkme = f.func()" << "int";
+
     QTest::newRow("with") << "with open('foo') as f: checkme = f.read()" << "str";
+    QTest::newRow("with_list_target") << "bar = [1, 2, 3]\n"
+                                         "with open('foo') as bar[1]: checkme = bar[1].read()" << "str";
+    QTest::newRow("with_attr_target") << "bar = object()\n"
+                                         "with open('foo') as bar.zep: checkme = bar.zep.read()" << "str";
+    QTest::newRow("with_nonself_enter") <<  // From https://bugs.kde.org/show_bug.cgi?id=399534
+        "class Mgr:\n"
+        "    def __enter__(self): return 42\n"
+        "    def __exit__(self, *args): pass\n"
+        "with Mgr() as asd:\n"
+        "    checkme = asd" << "int";
+    QTest::newRow("with_tuple_target") <<
+        "class Mgr:\n"
+        "    def __enter__(self): return (42, 3.4)\n"
+        "    def __exit__(self, *args): pass\n"
+        "with Mgr() as (aa, bb):\n"
+        "    checkme = bb" << "float";
+
     QTest::newRow("arg_after_vararg") << "def func(x, y, *, z:int): return z\ncheckme = func()" << "int";
     QTest::newRow("arg_after_vararg_with_default") << "def func(x=5, y=3, *, z:int): return z\ncheckme = func()" << "int";
 
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;;