diff --git a/roles/bootstrap-os/tasks/bootstrap-debian.yml b/roles/bootstrap-os/tasks/bootstrap-debian.yml
index ed43e89b4..625b43719 100644
--- a/roles/bootstrap-os/tasks/bootstrap-debian.yml
+++ b/roles/bootstrap-os/tasks/bootstrap-debian.yml
@@ -14,7 +14,7 @@
   tags: facts
 
 - name: Check http::proxy in /etc/apt/apt.conf
-  raw: grep -qs 'Acquire::http::proxy' /etc/apt/apt.conf
+  raw: grep -qsi 'Acquire::http::Proxy' /etc/apt/apt.conf
   register: need_http_proxy
   failed_when: false
   changed_when: false
@@ -22,14 +22,14 @@
   tags: facts
 
 - name: Add http_proxy to /etc/apt/apt.conf if http_proxy is defined
-  raw: echo 'Acquire::http::proxy "{{http_proxy}}";' >> /etc/apt/apt.conf
+  raw: echo 'Acquire::http::Proxy "{{http_proxy}}";' >> /etc/apt/apt.conf
   environment: {}
   when:
     - need_http_proxy.rc != 0
-    - https_proxy is defined
+    - http_proxy is defined
 
 - name: Check https::proxy in /etc/apt/apt.conf
-  raw: grep -qs 'Acquire::https::proxy' /etc/apt/apt.conf
+  raw: grep -qsi 'Acquire::https::Proxy' /etc/apt/apt.conf
   register: need_https_proxy
   failed_when: false
   changed_when: false
@@ -40,7 +40,7 @@
   raw: echo 'Acquire::https::proxy "{{https_proxy}}";' >> /etc/apt/apt.conf
   environment: {}
   when:
-    - need_http_proxy.rc != 0
+    - need_https_proxy.rc != 0
     - https_proxy is defined
 
 - name: Bootstrap | Install python 2.x, pip, and dbus