diff --git a/tools/oldest_constraints.txt b/tools/oldest_constraints.txt
index de2b83ad8..6722d7f15 100644
--- a/tools/oldest_constraints.txt
+++ b/tools/oldest_constraints.txt
@@ -43,7 +43,7 @@ oauth2client==2.0
 parsedatetime==1.3
 pyparsing==1.5.5
 python-digitalocean==1.11
-requests[security]==2.4.1
+requests[security]==2.20.0
 
 # Ubuntu Xenial constraints
 ConfigArgParse==0.10.0