diff --git a/docs/cspell.json b/docs/cspell.json
index bc2d4d46fb96b..8b28fd15e9c82 100644
--- a/docs/cspell.json
+++ b/docs/cspell.json
@@ -139,6 +139,7 @@
     "Mqgcq",
     "Multifactor",
     "Multihost",
+    "MYHOSTNAME",
     "Mzgz",
     "NOFILE",
     "NOKEY",
diff --git a/docs/pages/enroll-resources/machine-id/access-guides/ansible.mdx b/docs/pages/enroll-resources/machine-id/access-guides/ansible.mdx
index c38a8511ed672..2e2806a884d27 100644
--- a/docs/pages/enroll-resources/machine-id/access-guides/ansible.mdx
+++ b/docs/pages/enroll-resources/machine-id/access-guides/ansible.mdx
@@ -230,6 +230,34 @@ If `ssh` works, try running the playbook with verbose mode on:
 $ ansible-playbook -vvv playbook.yaml
 ```
 
+If your hostnames contain uppercase characters (like `MYHOSTNAME`), please note that Teleport's internal hostname matching
+is case sensitive by default, which can also lead to seeing this error.
+
+If this is the case, you can work around this by enabling case-insensitive routing at the cluster level.
+
+<Tabs>
+<TabItem label="Self-hosted Teleport">
+
+Edit your `/etc/teleport.yaml` config file on all servers running the Teleport `auth_service`, then restart Teleport on each.
+
+```yaml
+auth_service:
+  case_insensitive_routing: true
+```
+
+</TabItem>
+<TabItem label="Managed Teleport Enterprise/Cloud">
+
+Run `tctl edit cluster_networking_config` to add the following specification, then save and exit.
+
+```yaml
+spec:
+  case_insensitive_routing: true
+```
+
+</TabItem>
+</Tabs>
+
 ## Next steps
 
 - Read the [configuration reference](../../../reference/machine-id/configuration.mdx) to explore
diff --git a/docs/pages/enroll-resources/server-access/guides/ansible.mdx b/docs/pages/enroll-resources/server-access/guides/ansible.mdx
index 0d3d239fd4ba5..62d2327f66b6c 100644
--- a/docs/pages/enroll-resources/server-access/guides/ansible.mdx
+++ b/docs/pages/enroll-resources/server-access/guides/ansible.mdx
@@ -87,7 +87,7 @@ to a valid SSH username that works with the target host and is allowed by Telepo
 From the folder `ansible`, run the ansible playbook:
 
 ```code
-$ ansible-playbook playbook.yaml 
+$ ansible-playbook playbook.yaml
 
 # PLAY [all] *****************************************************************************************************************************************
 # TASK [Gathering Facts] *****************************************************************************************************************************
@@ -106,7 +106,7 @@ all ansible commands in the audit log.
 
 ## Troubleshooting
 
-In case if ansible can not connect, you may see error like this one:
+In cases where Ansible cannot connect, you may see an error like this:
 
 ```txt
 example.host | UNREACHABLE! => {
@@ -129,3 +129,31 @@ If `ssh` works, try running the playbook with verbose mode on:
 ```code
 $ ansible-playbook -vvvv playbook.yaml
 ```
+
+If your hostnames contain uppercase characters (like `MYHOSTNAME`), please note that Teleport's internal hostname matching
+is case sensitive by default, which can also lead to seeing this error.
+
+If this is the case, you can work around this by enabling case-insensitive routing at the cluster level.
+
+<Tabs>
+<TabItem label="Self-hosted Teleport">
+
+Edit your `/etc/teleport.yaml` config file on all servers running the Teleport `auth_service`, then restart Teleport on each.
+
+```yaml
+auth_service:
+  case_insensitive_routing: true
+```
+
+</TabItem>
+<TabItem label="Managed Teleport Enterprise/Cloud">
+
+Run `tctl edit cluster_networking_config` to add the following specification, then save and exit.
+
+```yaml
+spec:
+  case_insensitive_routing: true
+```
+
+</TabItem>
+</Tabs>
\ No newline at end of file