diff --git a/enos/enos-samples-ce-build.hcl b/enos/enos-samples-ce-build.hcl
index b87ab1b96b..8dd58ec822 100644
--- a/enos/enos-samples-ce-build.hcl
+++ b/enos/enos-samples-ce-build.hcl
@@ -97,7 +97,7 @@ sample "build_ce_linux_arm64_rpm" {
       arch            = ["arm64"]
       artifact_source = ["crt"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -107,7 +107,7 @@ sample "build_ce_linux_arm64_rpm" {
       arch            = ["arm64"]
       artifact_source = ["crt"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -117,7 +117,7 @@ sample "build_ce_linux_arm64_rpm" {
       arch            = ["arm64"]
       artifact_source = ["crt"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -127,7 +127,7 @@ sample "build_ce_linux_arm64_rpm" {
       arch            = ["arm64"]
       artifact_source = ["crt"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -141,7 +141,7 @@ sample "build_ce_linux_amd64_rpm" {
       arch            = ["amd64"]
       artifact_source = ["crt"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "leap", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "leap", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -151,7 +151,7 @@ sample "build_ce_linux_amd64_rpm" {
       arch            = ["amd64"]
       artifact_source = ["crt"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "leap", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "leap", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -161,7 +161,7 @@ sample "build_ce_linux_amd64_rpm" {
       arch            = ["amd64"]
       artifact_source = ["crt"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "leap", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "leap", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -171,7 +171,7 @@ sample "build_ce_linux_amd64_rpm" {
       arch            = ["amd64"]
       artifact_source = ["crt"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "leap", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "leap", "rhel", "sles"]
       edition         = ["ce"]
 
       exclude {
diff --git a/enos/enos-samples-ce-release.hcl b/enos/enos-samples-ce-release.hcl
index df194571bd..299a694934 100644
--- a/enos/enos-samples-ce-release.hcl
+++ b/enos/enos-samples-ce-release.hcl
@@ -97,7 +97,7 @@ sample "release_ce_linux_arm64_rpm" {
       arch            = ["arm64"]
       artifact_source = ["artifactory"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -107,7 +107,7 @@ sample "release_ce_linux_arm64_rpm" {
       arch            = ["arm64"]
       artifact_source = ["artifactory"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -117,7 +117,7 @@ sample "release_ce_linux_arm64_rpm" {
       arch            = ["arm64"]
       artifact_source = ["artifactory"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -127,7 +127,7 @@ sample "release_ce_linux_arm64_rpm" {
       arch            = ["arm64"]
       artifact_source = ["artifactory"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -141,7 +141,7 @@ sample "release_ce_linux_amd64_rpm" {
       arch            = ["amd64"]
       artifact_source = ["artifactory"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "leap", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "leap", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -151,7 +151,7 @@ sample "release_ce_linux_amd64_rpm" {
       arch            = ["amd64"]
       artifact_source = ["artifactory"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "leap", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "leap", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -161,7 +161,7 @@ sample "release_ce_linux_amd64_rpm" {
       arch            = ["amd64"]
       artifact_source = ["artifactory"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "leap", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "leap", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
@@ -171,7 +171,7 @@ sample "release_ce_linux_amd64_rpm" {
       arch            = ["amd64"]
       artifact_source = ["artifactory"]
       artifact_type   = ["package"]
-      distro          = ["amzn2", "leap", "rhel"] // temporarily remove SLES
+      distro          = ["amzn2", "leap", "rhel", "sles"]
       edition         = ["ce"]
     }
   }
diff --git a/enos/modules/install_packages/main.tf b/enos/modules/install_packages/main.tf
index f100678f59..e9f5977695 100644
--- a/enos/modules/install_packages/main.tf
+++ b/enos/modules/install_packages/main.tf
@@ -15,16 +15,15 @@ locals {
     "arm64" = "aarch64"
   }
   package_manager = {
-    # Note: though we generally use "amzn2" as our distro name for Amazon Linux 2, 
+    # Note: though we generally use "amzn2" as our distro name for Amazon Linux 2,
     # enos_host_info.hosts[each.key].distro returns "amzn", so that is what we reference here.
     "amzn"          = "yum"
     "opensuse-leap" = "zypper"
-    "rhel"          = "yum"
+    "rhel"          = "dnf"
     "sles"          = "zypper"
     "ubuntu"        = "apt"
   }
   distro_repos = {
-    # Currently sles is the only distro that requires setting up repos before installing packages
     "sles" = {
       "15.5" = "https://download.opensuse.org/repositories/network:utilities/SLE_15_SP5/network:utilities.repo"
     }
@@ -50,7 +49,7 @@ variable "hosts" {
 
 variable "timeout" {
   type        = number
-  description = "The max number of seconds to wait before timing out"
+  description = "The max number of seconds to wait before timing out. This is applied to each step so total timeout will be longer."
   default     = 120
 }
 
@@ -70,19 +69,20 @@ resource "enos_host_info" "hosts" {
   }
 }
 
-# Set up repos for each distro (in order to install some packages, some distros
-# require us to manually add the repo for that package first)
-resource "enos_remote_exec" "distro_repo_setup" {
+# Synchronize repositories on remote machines. This does not update packages but only ensures that
+# the remote hosts are configured with default upstream repositories that have been refreshed to
+# the latest metedata.
+resource "enos_remote_exec" "synchronize_repos" {
   for_each = var.hosts
 
   environment = {
     DISTRO          = enos_host_info.hosts[each.key].distro
-    DISTRO_REPOS    = try(local.distro_repos[enos_host_info.hosts[each.key].distro][enos_host_info.hosts[each.key].distro_version], "__none")
+    PACKAGE_MANAGER = local.package_manager[enos_host_info.hosts[each.key].distro]
     RETRY_INTERVAL  = var.retry_interval
     TIMEOUT_SECONDS = var.timeout
   }
 
-  scripts = [abspath("${path.module}/scripts/distro-repo-setup.sh")]
+  scripts = [abspath("${path.module}/scripts/synchronize-repos.sh")]
 
   transport = {
     ssh = {
@@ -91,9 +91,34 @@ resource "enos_remote_exec" "distro_repo_setup" {
   }
 }
 
-resource "enos_remote_exec" "install_packages" {
+# Add any additional repositories.
+resource "enos_remote_exec" "add_repos" {
   for_each   = var.hosts
-  depends_on = [enos_remote_exec.distro_repo_setup]
+  depends_on = [enos_remote_exec.synchronize_repos]
+
+  environment = {
+    DISTRO_REPOS    = try(local.distro_repos[enos_host_info.hosts[each.key].distro][enos_host_info.hosts[each.key].distro_version], "__none")
+    PACKAGE_MANAGER = local.package_manager[enos_host_info.hosts[each.key].distro]
+    RETRY_INTERVAL  = var.retry_interval
+    TIMEOUT_SECONDS = var.timeout
+  }
+
+  scripts = [abspath("${path.module}/scripts/add-repos.sh")]
+
+  transport = {
+    ssh = {
+      host = each.value.public_ip
+    }
+  }
+}
+
+# Install any required packages.
+resource "enos_remote_exec" "install_packages" {
+  for_each = var.hosts
+  depends_on = [
+    enos_remote_exec.synchronize_repos,
+    enos_remote_exec.add_repos,
+  ]
 
   environment = {
     PACKAGE_MANAGER = local.package_manager[enos_host_info.hosts[each.key].distro]
diff --git a/enos/modules/install_packages/scripts/add-repos.sh b/enos/modules/install_packages/scripts/add-repos.sh
new file mode 100644
index 0000000000..3f4ee881e2
--- /dev/null
+++ b/enos/modules/install_packages/scripts/add-repos.sh
@@ -0,0 +1,83 @@
+#!/usr/bin/env bash
+# Copyright (c) HashiCorp, Inc.
+# SPDX-License-Identifier: BUSL-1.1
+
+set -e
+
+fail() {
+  echo "$1" 1>&2
+  exit 1
+}
+
+[[ -z "${PACKAGE_MANAGER}" ]] && fail "PACKAGE_MANAGER env variable has not been set"
+[[ -z "${RETRY_INTERVAL}" ]] && fail "RETRY_INTERVAL env variable has not been set"
+[[ -z "${TIMEOUT_SECONDS}" ]] && fail "TIMEOUT_SECONDS env variable has not been set"
+
+# Add any repositories that have have been passed in
+add_repos() {
+  # If we don't have any repos on the list for this distro, no action needed.
+  if [ ${#DISTRO_REPOS[@]} -lt 1 ]; then
+    echo "DISTRO_REPOS is empty; No repos required for the packages for this Linux distro."
+    return 0
+  fi
+
+  case $PACKAGE_MANAGER in
+    apt)
+      # NOTE: We do not currently add any apt repositories in our scenarios. I suspect if that time
+      # comes we'll need to add support for apt-key here.
+      for repo in ${DISTRO_REPOS}; do
+        if [ "$repo" == "__none" ]; then
+          continue
+        fi
+        sudo add-apt-repository "${repo}"
+      done
+    ;;
+    dnf)
+      for repo in ${DISTRO_REPOS}; do
+        if [ "$repo" == "__none" ]; then
+          continue
+        fi
+        sudo dnf install -y "${repo}"
+        sudo dnf makecache -y
+      done
+    ;;
+    yum)
+      for repo in ${DISTRO_REPOS}; do
+        if [ "$repo" == "__none" ]; then
+          continue
+        fi
+        sudo yum install -y "${repo}"
+        sudo yum makecache -y
+      done
+    ;;
+    zypper)
+      # Add each repo
+      for repo in ${DISTRO_REPOS}; do
+        if [ "$repo" == "__none" ]; then
+          continue
+        fi
+        if sudo zypper lr "${repo}"; then
+          echo "A repo named ${repo} already exists, skipping..."
+          continue
+        fi
+        sudo zypper --gpg-auto-import-keys --non-interactive addrepo "${repo}"
+      done
+      sudo zypper --gpg-auto-import-keys ref
+      sudo zypper --gpg-auto-import-keys refs
+    ;;
+    *)
+      fail "Unsupported package manager: ${PACKAGE_MANAGER}"
+  esac
+}
+
+begin_time=$(date +%s)
+end_time=$((begin_time + TIMEOUT_SECONDS))
+while [ "$(date +%s)" -lt "$end_time" ]; do
+  if add_repos; then
+    exit 0
+  fi
+
+  sleep "$RETRY_INTERVAL"
+done
+
+fail "Timed out waiting for distro repos to be set up"
diff --git a/enos/modules/install_packages/scripts/distro-repo-setup.sh b/enos/modules/install_packages/scripts/distro-repo-setup.sh
deleted file mode 100644
index 512cdedf10..0000000000
--- a/enos/modules/install_packages/scripts/distro-repo-setup.sh
+++ /dev/null
@@ -1,57 +0,0 @@
-#!/usr/bin/env bash
-# Copyright (c) HashiCorp, Inc.
-# SPDX-License-Identifier: BUSL-1.1
-
-set -e
-
-fail() {
-  echo "$1" 1>&2
-  exit 1
-}
-
-[[ -z "$DISTRO" ]] && fail "DISTRO env variable has not been set"
-[[ -z "$RETRY_INTERVAL" ]] && fail "RETRY_INTERVAL env variable has not been set"
-[[ -z "$TIMEOUT_SECONDS" ]] && fail "TIMEOUT_SECONDS env variable has not been set"
-
-setup_repos() {
-  # If we don't have any repos on the list for this distro, no action needed.
-  if [ ${#DISTRO_REPOS[@]} -lt 1 ]; then
-    echo "DISTRO_REPOS is empty; No repos required for the packages for this Linux distro."
-    return 0
-  fi
-
-  # Wait for cloud-init to finish so it doesn't race with any of our package installations.
-  # Note: Amazon Linux 2 throws Python 2.7 errors when running `cloud-init status` as
-  # non-root user (known bug).
-  sudo cloud-init status --wait
-
-  case $DISTRO in
-    "sles")
-      for repo in ${DISTRO_REPOS}; do
-        sudo zypper addrepo "${repo}"
-      done
-      ;;
-    "rhel")
-      for repo in ${DISTRO_REPOS}; do
-        sudo rm -r /var/cache/dnf
-        sudo dnf install -y "${repo}"
-        sudo dnf update -y --refresh
-      done
-      ;;
-    *)
-      return
-      ;;
-  esac
-}
-
-begin_time=$(date +%s)
-end_time=$((begin_time + TIMEOUT_SECONDS))
-while [ "$(date +%s)" -lt "$end_time" ]; do
-  if setup_repos; then
-    exit 0
-  fi
-
-  sleep "$RETRY_INTERVAL"
-done
-
-fail "Timed out waiting for distro repos to install"
diff --git a/enos/modules/install_packages/scripts/install-packages.sh b/enos/modules/install_packages/scripts/install-packages.sh
index 99ac4a8a76..cb771d2b9d 100644
--- a/enos/modules/install_packages/scripts/install-packages.sh
+++ b/enos/modules/install_packages/scripts/install-packages.sh
@@ -14,59 +14,81 @@ fail() {
 [[ -z "${PACKAGES}" ]] && fail "PACKAGES env variable has not been set"
 [[ -z "${PACKAGE_MANAGER}" ]] && fail "PACKAGE_MANAGER env variable has not been set"
 
+# Install packages based on the provided packages and package manager. We assume that the repositories
+# have already been synchronized by the repo setup that is a prerequisite for this script.
 install_packages() {
   if [[ "${PACKAGES}" = "__skip" ]]; then
     return 0
-  fi 
+  fi
 
   set -x
   echo "Installing Dependencies: ${PACKAGES}"
 
   # Use the default package manager of the current Linux distro to install packages
   case $PACKAGE_MANAGER in
-
-    "apt")
-      sudo apt update
+    apt)
       for package in ${PACKAGES}; do
         if dpkg -s "${package}"; then
+          echo "Skipping installation of ${package} because it is already installed"
           continue
         else
           echo "Installing ${package}"
-          sudo apt install -y "${package}"
+          local output
+          if ! output=$(sudo apt install -y "${package}" 2>&1); then
+            echo "Failed to install ${package}: ${output}" 1>&2
+            return 1
+          fi
         fi
       done
-      ;;
-
-    "yum")
+    ;;
+    dnf)
       for package in ${PACKAGES}; do
         if rpm -q "${package}"; then
+          echo "Skipping installation of ${package} because it is already installed"
           continue
         else
           echo "Installing ${package}"
-          sudo yum -y install "${package}"
+          local output
+          if ! output=$(sudo dnf -y install "${package}" 2>&1); then
+            echo "Failed to install ${package}: ${output}" 1>&2
+            return 1
+          fi
         fi
       done
-      ;;
-
-    "zypper")
-      cd /tmp
-      sudo zypper --gpg-auto-import-keys ref
+    ;;
+    yum)
       for package in ${PACKAGES}; do
         if rpm -q "${package}"; then
+          echo "Skipping installation of ${package} because it is already installed"
           continue
         else
           echo "Installing ${package}"
-          sudo zypper --non-interactive install "${package}"
-          date
+          local output
+          if ! output=$(sudo yum -y install "${package}" 2>&1); then
+            echo "Failed to install ${package}: ${output}" 1>&2
+            return 1
+          fi
         fi
-        sudo zypper search -i
       done
-      ;;
-
+    ;;
+    zypper)
+      for package in ${PACKAGES}; do
+        if rpm -q "${package}"; then
+          echo "Skipping installation of ${package} because it is already installed"
+          continue
+        else
+          echo "Installing ${package}"
+          local output
+          if ! output=$(sudo zypper --non-interactive install -y -l --force-resolution "${package}" 2>&1); then
+            echo "Failed to install ${package}: ${output}" 1>&2
+            return 1
+          fi
+        fi
+      done
+    ;;
     *)
       fail "No matching package manager provided."
-      ;;
-
+    ;;
   esac
 }
 
diff --git a/enos/modules/install_packages/scripts/synchronize-repos.sh b/enos/modules/install_packages/scripts/synchronize-repos.sh
new file mode 100644
index 0000000000..034b04b90d
--- /dev/null
+++ b/enos/modules/install_packages/scripts/synchronize-repos.sh
@@ -0,0 +1,118 @@
+#!/usr/bin/env bash
+# Copyright (c) HashiCorp, Inc.
+# SPDX-License-Identifier: BUSL-1.1
+
+set -e
+
+fail() {
+  echo "$1" 1>&2
+  exit 1
+}
+
+[[ -z "${PACKAGE_MANAGER}" ]] && fail "PACKAGE_MANAGER env variable has not been set"
+[[ -z "${RETRY_INTERVAL}" ]] && fail "RETRY_INTERVAL env variable has not been set"
+[[ -z "${TIMEOUT_SECONDS}" ]] && fail "TIMEOUT_SECONDS env variable has not been set"
+
+# The SLES AMI's do not come configured with Zypper repositories by default. To get them you
+# have to run SUSEConnect to register the instance with SUSE. On the AMI this is handled
+# automatically by a oneshot systemd unit called guestregister.service. This oneshot service needs
+# to complete before any other repo or package steps are completed. At the time of writing it's very
+# unreliable so we have to ensure that it has correctly executed ourselves or restart it. We do this
+# by checking if the guestregister.service has reached the correct "inactive" state that we need.
+# If it hasn't reached that state it's usually in some sort of active state, i.e. running, or it has
+# failed. If it's in one of the active states we need to let it continue and check the status when
+# it completes. If it has completed but is failed we'll restart the service to re-run the script that
+# executes SUSEConnect.
+sles_check_guestregister_service_and_restart_if_failed() {
+  local active_state
+  local failed_state
+
+  # systemctl returns non-zero exit codes. We rely on output here because all states don't have
+  # their own exit code.
+  set +e
+  active_state=$(sudo systemctl is-active guestregister.service)
+  failed_state=$(sudo systemctl is-failed guestregister.service)
+  set -e
+
+  case "$active_state" in
+    active|activating|deactivating)
+      # It's running so we'll return 1 and get retried by the caller
+      echo "the guestregister.service is still in the ${active_state} state" 1>&2
+      return 1
+    ;;
+    *)
+      if [ "$active_state" == "inactive" ] && [ "$failed_state" == "inactive" ]; then
+        # The oneshot has completed and hasn't "failed"
+        echo "the guestregister.service is 'inactive' for both active and failed states"
+        return 0
+      fi
+
+      # Our service is stopped and failed, restart it and hope it works the next time
+      sudo systemctl restart --wait guestregister.service
+    ;;
+  esac
+}
+
+# Check or restart the guestregister service if it has failed. If it passes do another check to make
+# sure that the zypper repositories list isn't empty.
+sles_ensure_suseconnect() {
+  local health_output
+  if ! health_output=$(sles_check_guestregister_service_and_restart_if_failed); then
+    echo "the guestregister.service failed to reach a healthy state: ${health_output}" 1>&2
+    return 1
+  fi
+
+  # Make sure Zypper has repositories.
+  if ! lr_output=$(zypper lr); then
+    echo "The guestregister.service failed. Unable to SUSEConnect and thus have no Zypper repositories: ${lr_output}: ${health_output}." 1>&2
+    return 1
+  fi
+
+  return 0
+}
+
+# Synchronize our repositories so that futher installation steps are working with updated cache
+# and repo metadata.
+synchronize_repos() {
+  case $PACKAGE_MANAGER in
+    apt)
+      sudo apt update
+    ;;
+    dnf)
+      sudo dnf makecache
+    ;;
+    yum)
+      sudo yum makecache
+    ;;
+    zypper)
+      if [ "$DISTRO" == "sles" ]; then
+        if ! sles_ensure_suseconnect; then
+          return 1
+        fi
+      fi
+      sudo zypper --gpg-auto-import-keys --non-interactive ref
+      sudo zypper --gpg-auto-import-keys --non-interactive refs
+      ;;
+    *)
+      return 0
+    ;;
+  esac
+}
+
+# Before we start to modify repositories and install packages we'll wait for cloud-init to finish
+# so it doesn't race with any of our package installations.
+# We run as sudo becase Amazon Linux 2 throws Python 2.7 errors when running `cloud-init status` as
+# non-root user (known bug).
+sudo cloud-init status --wait
+
+begin_time=$(date +%s)
+end_time=$((begin_time + TIMEOUT_SECONDS))
+while [ "$(date +%s)" -lt "$end_time" ]; do
+  if synchronize_repos; then
+    exit 0
+  fi
+
+  sleep "$RETRY_INTERVAL"
+done
+
+fail "Timed out waiting for distro repos to be set up"