diff --git a/Dockerfile b/Dockerfile
index ce0eeda46..ece04b6e0 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -84,6 +84,8 @@ RUN apt-get update && \
     apt-get install -y --no-install-recommends libxmlsec1-openssl libmaxminddb0 && \
     # Required for bootstrap & healtcheck
     apt-get install -y --no-install-recommends runit && \
+    # Required for outposts
+    apt-get install -y --no-install-recommends openssh-client && \
     pip install --no-cache-dir -r /requirements.txt && \
     apt-get remove --purge -y build-essential pkg-config libxmlsec1-dev && \
     apt-get autoremove --purge -y && \
diff --git a/authentik/outposts/controllers/docker.py b/authentik/outposts/controllers/docker.py
index 48918e25e..28da249da 100644
--- a/authentik/outposts/controllers/docker.py
+++ b/authentik/outposts/controllers/docker.py
@@ -58,6 +58,7 @@ class DockerClient(UpstreamDockerClient, BaseClient):
                 super().__init__(
                     base_url=connection.url,
                     tls=tls_config,
+                    use_ssh_client=True,
                 )
             except SSHException as exc:
                 if self.ssh:
diff --git a/poetry.lock b/poetry.lock
index 0930f346a..02bd05dd4 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.4.2 and should not be changed by hand.
 
 [[package]]
 name = "aiohttp"
@@ -406,41 +406,6 @@ test = ["beautifulsoup4 (>=4.8.0)", "coverage (>=4.5.4)", "fixtures (>=3.0.0)",
 toml = ["tomli (>=1.1.0)"]
 yaml = ["PyYAML"]
 
-[[package]]
-name = "bcrypt"
-version = "4.0.1"
-description = "Modern password hashing for your software and your servers"
-category = "main"
-optional = false
-python-versions = ">=3.6"
-files = [
-    {file = "bcrypt-4.0.1-cp36-abi3-macosx_10_10_universal2.whl", hash = "sha256:b1023030aec778185a6c16cf70f359cbb6e0c289fd564a7cfa29e727a1c38f8f"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.manylinux_2_24_aarch64.whl", hash = "sha256:08d2947c490093a11416df18043c27abe3921558d2c03e2076ccb28a116cb6d0"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:0eaa47d4661c326bfc9d08d16debbc4edf78778e6aaba29c1bc7ce67214d4410"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:ae88eca3024bb34bb3430f964beab71226e761f51b912de5133470b649d82344"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_24_x86_64.whl", hash = "sha256:a522427293d77e1c29e303fc282e2d71864579527a04ddcfda6d4f8396c6c36a"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_28_aarch64.whl", hash = "sha256:fbdaec13c5105f0c4e5c52614d04f0bca5f5af007910daa8b6b12095edaa67b3"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_28_x86_64.whl", hash = "sha256:ca3204d00d3cb2dfed07f2d74a25f12fc12f73e606fcaa6975d1f7ae69cacbb2"},
-    {file = "bcrypt-4.0.1-cp36-abi3-musllinux_1_1_aarch64.whl", hash = "sha256:089098effa1bc35dc055366740a067a2fc76987e8ec75349eb9484061c54f535"},
-    {file = "bcrypt-4.0.1-cp36-abi3-musllinux_1_1_x86_64.whl", hash = "sha256:e9a51bbfe7e9802b5f3508687758b564069ba937748ad7b9e890086290d2f79e"},
-    {file = "bcrypt-4.0.1-cp36-abi3-win32.whl", hash = "sha256:2caffdae059e06ac23fce178d31b4a702f2a3264c20bfb5ff541b338194d8fab"},
-    {file = "bcrypt-4.0.1-cp36-abi3-win_amd64.whl", hash = "sha256:8a68f4341daf7522fe8d73874de8906f3a339048ba406be6ddc1b3ccb16fc0d9"},
-    {file = "bcrypt-4.0.1-pp37-pypy37_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:bf4fa8b2ca74381bb5442c089350f09a3f17797829d958fad058d6e44d9eb83c"},
-    {file = "bcrypt-4.0.1-pp37-pypy37_pp73-manylinux_2_24_x86_64.whl", hash = "sha256:67a97e1c405b24f19d08890e7ae0c4f7ce1e56a712a016746c8b2d7732d65d4b"},
-    {file = "bcrypt-4.0.1-pp37-pypy37_pp73-manylinux_2_28_x86_64.whl", hash = "sha256:b3b85202d95dd568efcb35b53936c5e3b3600c7cdcc6115ba461df3a8e89f38d"},
-    {file = "bcrypt-4.0.1-pp38-pypy38_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:cbb03eec97496166b704ed663a53680ab57c5084b2fc98ef23291987b525cb7d"},
-    {file = "bcrypt-4.0.1-pp38-pypy38_pp73-manylinux_2_24_x86_64.whl", hash = "sha256:5ad4d32a28b80c5fa6671ccfb43676e8c1cc232887759d1cd7b6f56ea4355215"},
-    {file = "bcrypt-4.0.1-pp38-pypy38_pp73-manylinux_2_28_x86_64.whl", hash = "sha256:b57adba8a1444faf784394de3436233728a1ecaeb6e07e8c22c8848f179b893c"},
-    {file = "bcrypt-4.0.1-pp39-pypy39_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:705b2cea8a9ed3d55b4491887ceadb0106acf7c6387699fca771af56b1cdeeda"},
-    {file = "bcrypt-4.0.1-pp39-pypy39_pp73-manylinux_2_24_x86_64.whl", hash = "sha256:2b3ac11cf45161628f1f3733263e63194f22664bf4d0c0f3ab34099c02134665"},
-    {file = "bcrypt-4.0.1-pp39-pypy39_pp73-manylinux_2_28_x86_64.whl", hash = "sha256:3100851841186c25f127731b9fa11909ab7b1df6fc4b9f8353f4f1fd952fbf71"},
-    {file = "bcrypt-4.0.1.tar.gz", hash = "sha256:27d375903ac8261cfe4047f6709d16f7d18d39b1ec92aaf72af989552a650ebd"},
-]
-
-[package.extras]
-tests = ["pytest (>=3.2.1,!=3.3.0)"]
-typecheck = ["mypy"]
-
 [[package]]
 name = "billiard"
 version = "3.6.4.0"
@@ -2238,28 +2203,6 @@ files = [
     {file = "packaging-23.1.tar.gz", hash = "sha256:a392980d2b6cffa644431898be54b0045151319d1e7ec34f0cfed48767dd334f"},
 ]
 
-[[package]]
-name = "paramiko"
-version = "3.1.0"
-description = "SSH2 protocol library"
-category = "main"
-optional = false
-python-versions = ">=3.6"
-files = [
-    {file = "paramiko-3.1.0-py3-none-any.whl", hash = "sha256:f0caa660e797d9cd10db6fc6ae81e2c9b2767af75c3180fcd0e46158cd368d7f"},
-    {file = "paramiko-3.1.0.tar.gz", hash = "sha256:6950faca6819acd3219d4ae694a23c7a87ee38d084f70c1724b0c0dbb8b75769"},
-]
-
-[package.dependencies]
-bcrypt = ">=3.2"
-cryptography = ">=3.3"
-pynacl = ">=1.5"
-
-[package.extras]
-all = ["gssapi (>=1.4.1)", "invoke (>=2.0)", "pyasn1 (>=0.1.7)", "pywin32 (>=2.1.8)"]
-gssapi = ["gssapi (>=1.4.1)", "pyasn1 (>=0.1.7)", "pywin32 (>=2.1.8)"]
-invoke = ["invoke (>=2.0)"]
-
 [[package]]
 name = "pathspec"
 version = "0.10.2"
@@ -2677,33 +2620,6 @@ files = [
 [package.dependencies]
 pylint = ">=1.7"
 
-[[package]]
-name = "pynacl"
-version = "1.5.0"
-description = "Python binding to the Networking and Cryptography (NaCl) library"
-category = "main"
-optional = false
-python-versions = ">=3.6"
-files = [
-    {file = "PyNaCl-1.5.0-cp36-abi3-macosx_10_10_universal2.whl", hash = "sha256:401002a4aaa07c9414132aaed7f6836ff98f59277a234704ff66878c2ee4a0d1"},
-    {file = "PyNaCl-1.5.0-cp36-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.manylinux_2_24_aarch64.whl", hash = "sha256:52cb72a79269189d4e0dc537556f4740f7f0a9ec41c1322598799b0bdad4ef92"},
-    {file = "PyNaCl-1.5.0-cp36-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:a36d4a9dda1f19ce6e03c9a784a2921a4b726b02e1c736600ca9c22029474394"},
-    {file = "PyNaCl-1.5.0-cp36-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.manylinux_2_24_x86_64.whl", hash = "sha256:0c84947a22519e013607c9be43706dd42513f9e6ae5d39d3613ca1e142fba44d"},
-    {file = "PyNaCl-1.5.0-cp36-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:06b8f6fa7f5de8d5d2f7573fe8c863c051225a27b61e6860fd047b1775807858"},
-    {file = "PyNaCl-1.5.0-cp36-abi3-musllinux_1_1_aarch64.whl", hash = "sha256:a422368fc821589c228f4c49438a368831cb5bbc0eab5ebe1d7fac9dded6567b"},
-    {file = "PyNaCl-1.5.0-cp36-abi3-musllinux_1_1_x86_64.whl", hash = "sha256:61f642bf2378713e2c2e1de73444a3778e5f0a38be6fee0fe532fe30060282ff"},
-    {file = "PyNaCl-1.5.0-cp36-abi3-win32.whl", hash = "sha256:e46dae94e34b085175f8abb3b0aaa7da40767865ac82c928eeb9e57e1ea8a543"},
-    {file = "PyNaCl-1.5.0-cp36-abi3-win_amd64.whl", hash = "sha256:20f42270d27e1b6a29f54032090b972d97f0a1b0948cc52392041ef7831fee93"},
-    {file = "PyNaCl-1.5.0.tar.gz", hash = "sha256:8ac7448f09ab85811607bdd21ec2464495ac8b7c66d146bf545b0f08fb9220ba"},
-]
-
-[package.dependencies]
-cffi = ">=1.4.1"
-
-[package.extras]
-docs = ["sphinx (>=1.6.5)", "sphinx-rtd-theme"]
-tests = ["hypothesis (>=3.27.0)", "pytest (>=3.2.1,!=3.3.0)"]
-
 [[package]]
 name = "pyopenssl"
 version = "23.0.0"
@@ -4152,4 +4068,4 @@ files = [
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.11"
-content-hash = "82fc267d6041997d1410a951033cdb9f6c57d91df7d48acaecdbab320daab58e"
+content-hash = "78316d0e5e830f8c8ef73e654bb900b51e628759ec36698b0cf3153ba393f903"
diff --git a/pyproject.toml b/pyproject.toml
index 56c4284d1..d14bf933d 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -146,7 +146,6 @@ ldap3 = "*"
 lxml = "*"
 opencontainers = { extras = ["reggie"], version = "*" }
 packaging = "*"
-paramiko = "*"
 psycopg2-binary = "*"
 pycryptodome = "*"
 pyjwt = "*"