diff --git a/certbot/docs/install.rst b/certbot/docs/install.rst
index 308cab697..5d083ae17 100644
--- a/certbot/docs/install.rst
+++ b/certbot/docs/install.rst
@@ -250,9 +250,6 @@ through a command like:
 They can be installed by running the same installation command above but
 replacing ``certbot`` with the name of the desired package.
 
-There are no Certbot packages available for Debian Jessie and Jessie users
-should instead use certbot-auto_.
-
 **Ubuntu**
 
 If you run Ubuntu Trusty, Xenial, or Bionic, certbot is available through the official PPA,
diff --git a/certbot/docs/using.rst b/certbot/docs/using.rst
index 89cdb7d51..c2c0910e5 100644
--- a/certbot/docs/using.rst
+++ b/certbot/docs/using.rst
@@ -631,7 +631,6 @@ systemd timers (`systemctl list-timers`).
    :header: "Distribution Name", "Distribution Version", "Automation Method"
 
    "CentOS", "EPEL 7", "systemd"
-   "Debian", "jessie", "cron, systemd"
    "Debian", "stretch", "cron, systemd"
    "Debian", "testing/sid", "cron, systemd"
    "Fedora", "26", "systemd"
diff --git a/letsencrypt-auto-source/rebuild_dependencies.py b/letsencrypt-auto-source/rebuild_dependencies.py
index a28fa2693..9fc0ff324 100755
--- a/letsencrypt-auto-source/rebuild_dependencies.py
+++ b/letsencrypt-auto-source/rebuild_dependencies.py
@@ -27,7 +27,7 @@ import argparse
 # The list of docker distributions to test dependencies against with.
 DISTRIBUTION_LIST = [
     'ubuntu:18.04', 'ubuntu:16.04',
-    'debian:stretch', 'debian:jessie',
+    'debian:stretch',
     'centos:7', 'centos:6',
     'opensuse/leap:15',
     'fedora:29',
diff --git a/tests/letstest/apache2_targets.yaml b/tests/letstest/apache2_targets.yaml
index d0a682bae..19411435c 100644
--- a/tests/letstest/apache2_targets.yaml
+++ b/tests/letstest/apache2_targets.yaml
@@ -36,11 +36,6 @@ targets:
     virt: hvm
     user: admin
     machine_type: a1.medium
-  - ami: ami-077bf3962f29d3fa4
-    name: debian8.1
-    type: ubuntu
-    virt: hvm
-    user: admin
   #-----------------------------------------------------------------------------
   # Fedora
   - ami: ami-0fcbe88944a53b4c8
diff --git a/tests/letstest/targets.yaml b/tests/letstest/targets.yaml
index 2cda2d6ef..9daba3910 100644
--- a/tests/letstest/targets.yaml
+++ b/tests/letstest/targets.yaml
@@ -36,11 +36,6 @@ targets:
     virt: hvm
     user: admin
     machine_type: a1.medium
-  - ami: ami-077bf3962f29d3fa4
-    name: debian8.1
-    type: ubuntu
-    virt: hvm
-    user: admin
     # userdata: |
     #   #cloud-init
     #   runcmd:
diff --git a/tools/oldest_constraints.txt b/tools/oldest_constraints.txt
index 5145e3ddf..1f415dd4c 100644
--- a/tools/oldest_constraints.txt
+++ b/tools/oldest_constraints.txt
@@ -26,6 +26,9 @@ zope.event==4.0.3
 zope.interface==4.0.5
 
 # Debian Jessie Backports constraints
+# Debian Jessie has reached end of life. However:
+# When it becomes necessary to upgrade any of these dependencies, you should only update them to the oldest version of the package found
+# in a non-EOL'd version of CentOS, Debian, or Ubuntu that has Certbot packages in their OS repositories.
 PyICU==1.8
 colorama==0.3.2
 enum34==1.0.3