diff --git a/REST/bash/Targets/ListeningLinuxTentacleStopTrustingOldOctopusServerCert.sh b/REST/bash/Targets/ListeningLinuxTentacleStopTrustingOldOctopusServerCert.sh
new file mode 100644
index 00000000..fcfaaf92
--- /dev/null
+++ b/REST/bash/Targets/ListeningLinuxTentacleStopTrustingOldOctopusServerCert.sh
@@ -0,0 +1,11 @@
+# Run on *each* Linux Listening Tentacle VM
+
+# Stop trusting the old certificate
+echo "Stop trusting the old Octopus Server certificate..."
+sudo ./Tentacle configure --instance Tentacle --remove-trust <old-thumbprint>
+echo "Successfully completed removing the old Octopus Server certificate"
+
+# Restart the Tentacle service
+echo "Restarting the Tentacle service..."
+sudo ./Tentacle service --instance Tentacle --restart
+echo "Successfully completed restarting the Tentacle service"
diff --git a/REST/bash/Targets/ListeningLinuxTentacleTrustNewCert.sh b/REST/bash/Targets/ListeningLinuxTentacleTrustNewCert.sh
new file mode 100644
index 00000000..76db3134
--- /dev/null
+++ b/REST/bash/Targets/ListeningLinuxTentacleTrustNewCert.sh
@@ -0,0 +1,8 @@
+# Run on *each* Linux Listening Tentacle VM
+
+# Trust new Octopus Server thumbprint
+echo "Trust the new Octopus Server certificate / thumbprint..."
+sudo ./Tentacle configure --trust="<new-octopus-server-thumbprint>"
+echo "Successfully completed trusting the Octopus Server certificate / thumbprint."
+
+echo "Don't forget, you'll need to come back later and run the script to *stop* trusting the old Octopus Server certificate & thumbprint..."
diff --git a/REST/bash/Targets/PollingLinuxTentacleTrustNewCert.sh b/REST/bash/Targets/PollingLinuxTentacleTrustNewCert.sh
new file mode 100644
index 00000000..43ea5016
--- /dev/null
+++ b/REST/bash/Targets/PollingLinuxTentacleTrustNewCert.sh
@@ -0,0 +1,8 @@
+# Run on *each* Linux Polling Tentacle VM
+
+# ** Note: There will be down time in comms with your Polling Tentacles until after you have completed running this script on *each* VM where a Polling Tentacle is installed. **
+
+# Trust new Octopus Server thumbprint
+echo "Trust the new Octopus Server certificate / thumbprint..."
+sudo ./Tentacle update-trust --oldThumbprint "1111111111111111111111111111111111111111" --newThumbprint "1234567890123456789012345678901234567890"
+echo "Successfully completed trusting the Octopus Server certificate / thumbprint."