diff --git a/authentik/outposts/controllers/docker.py b/authentik/outposts/controllers/docker.py
index ed10dcb7f..af4c08651 100644
--- a/authentik/outposts/controllers/docker.py
+++ b/authentik/outposts/controllers/docker.py
@@ -15,7 +15,7 @@ from yaml import safe_dump
 
 from authentik import __version__
 from authentik.outposts.controllers.base import BaseClient, BaseController, ControllerException
-from authentik.outposts.docker_ssh import DockerInlineSSH
+from authentik.outposts.docker_ssh import DockerInlineSSH, SSHManagedExternallyException
 from authentik.outposts.docker_tls import DockerInlineTLS
 from authentik.outposts.managed import MANAGED_OUTPOST
 from authentik.outposts.models import (
@@ -35,6 +35,7 @@ class DockerClient(UpstreamDockerClient, BaseClient):
     def __init__(self, connection: DockerServiceConnection):
         self.tls = None
         self.ssh = None
+        self.logger = get_logger()
         if connection.local:
             # Same result as DockerClient.from_env
             super().__init__(**kwargs_from_env())
@@ -42,8 +43,12 @@ class DockerClient(UpstreamDockerClient, BaseClient):
             parsed_url = urlparse(connection.url)
             tls_config = False
             if parsed_url.scheme == "ssh":
-                self.ssh = DockerInlineSSH(parsed_url.hostname, connection.tls_authentication)
-                self.ssh.write()
+                try:
+                    self.ssh = DockerInlineSSH(parsed_url.hostname, connection.tls_authentication)
+                    self.ssh.write()
+                except SSHManagedExternallyException as exc:
+                    # SSH config is managed externally
+                    self.logger.info(f"SSH Managed externally: {exc}")
             else:
                 self.tls = DockerInlineTLS(
                     verification_kp=connection.tls_verification,
@@ -57,7 +62,6 @@ class DockerClient(UpstreamDockerClient, BaseClient):
                 )
             except SSHException as exc:
                 raise ServiceConnectionInvalid from exc
-        self.logger = get_logger()
         # Ensure the client actually works
         self.containers.list()
 
diff --git a/authentik/outposts/docker_ssh.py b/authentik/outposts/docker_ssh.py
index 929f55e34..657e38a76 100644
--- a/authentik/outposts/docker_ssh.py
+++ b/authentik/outposts/docker_ssh.py
@@ -16,6 +16,10 @@ def opener(path, flags):
     return os.open(path, flags, 0o700)
 
 
+class SSHManagedExternallyException(DockerException):
+    """Raised when the ssh config file is managed externally."""
+
+
 class DockerInlineSSH:
     """Create paramiko ssh config from CertificateKeyPair"""
 
@@ -29,9 +33,15 @@ class DockerInlineSSH:
     def __init__(self, host: str, keypair: CertificateKeyPair) -> None:
         self.host = host
         self.keypair = keypair
+        self.config_path = Path("~/.ssh/config").expanduser()
+        if self.config_path.exists() and HEADER not in self.config_path.read_text(encoding="utf-8"):
+            # SSH Config file already exists and there's no header from us, meaning that it's
+            # been externally mapped into the container for more complex configs
+            raise SSHManagedExternallyException(
+                "SSH Config exists and does not contain authentik header"
+            )
         if not self.keypair:
             raise DockerException("keypair must be set for SSH connections")
-        self.config_path = Path("~/.ssh/config").expanduser()
         self.header = f"{HEADER} - {self.host}\n"
 
     def write_config(self, key_path: str) -> bool: