diff --git a/jedi/third_party/README_typeshed.md b/jedi/third_party/README_typeshed.md
index 516b030e..60ae79df 100644
--- a/jedi/third_party/README_typeshed.md
+++ b/jedi/third_party/README_typeshed.md
@@ -12,3 +12,19 @@ https://github.com/davidhalter/typeshed.git for two reasons:
 
 - Jedi doesn't understand Tuple.__init__ properly.
 - Typeshed has a bug: https://github.com/python/typeshed/issues/2999
+
+Therefore we need a bit of a complicated process to upgrade typeshed:
+
+    cd jedi/third_party/typeshed
+    git remote add upstream https://github.com/python/typeshed
+    git fetch upstream
+    git checkout jedi
+    git rebase upstream/master
+    git push -f
+
+    git push
+    cd ../../..
+    git commit jedi/third_party/typeshed -m "Upgrade typeshed"
+
+If merge conflicts appear, just make sure that only one commit from Jedi
+appears.
diff --git a/jedi/third_party/typeshed b/jedi/third_party/typeshed
index ff92f09e..d3864524 160000
--- a/jedi/third_party/typeshed
+++ b/jedi/third_party/typeshed
@@ -1 +1 @@
-Subproject commit ff92f09efbe9c7d67ca13d30ca56c4afbe13f129
+Subproject commit d38645247816f862cafeed21a8f4466d306aacf3
diff --git a/test/completion/stdlib.py b/test/completion/stdlib.py
index ba617fea..5bd20c25 100644
--- a/test/completion/stdlib.py
+++ b/test/completion/stdlib.py
@@ -190,6 +190,10 @@ def huhu(db):
     #? sqlite3.Connection()
     db
 
+with sqlite3.connect() as c:
+    #? sqlite3.Connection()
+    c
+
 # -----------------
 # hashlib
 # -----------------