diff --git a/infrastructure/containers/vpn/makefile b/infrastructure/containers/vpn/makefile
new file mode 100644
index 00000000..ed88c4d8
--- /dev/null
+++ b/infrastructure/containers/vpn/makefile
@@ -0,0 +1,2 @@
+install:
+	pip install -e .
diff --git a/infrastructure/containers/vpn/rootski_vpn/__init__.py b/infrastructure/containers/vpn/rootski_vpn/__init__.py
new file mode 100644
index 00000000..585e4498
--- /dev/null
+++ b/infrastructure/containers/vpn/rootski_vpn/__init__.py
@@ -0,0 +1 @@
+"""Generate the server config file for the Rootski Vpn."""
diff --git a/infrastructure/containers/vpn/rootski_vpn/generate_server_conf.py b/infrastructure/containers/vpn/rootski_vpn/generate_server_conf.py
new file mode 100644
index 00000000..37207feb
--- /dev/null
+++ b/infrastructure/containers/vpn/rootski_vpn/generate_server_conf.py
@@ -0,0 +1,217 @@
+"""
+Standalone shell script for generating the secrets and configuration file for the wireguard server.
+
+This script generates the necessary files (wg0.conf, server.key, and server.pub) to run a wireguard server
+on a lightsail instance. This file is used by wireguard_vpn.py in the
+rootski/infrastructure/iac/aws-cdk/backend/rootski_backend_cdk/lightsail_vpn folder.
+"""
+
+import json
+from pathlib import Path
+from textwrap import dedent
+from typing import Dict, List
+
+import boto3
+
+
+def main():
+    """Genereate files for the server configuration, server private key, and server public key."""
+    key_pairs: List[dict] = fetch_key_pairs_from_ssm(
+        key_pairs_ssm_prefix="/rootski/wireguard-vpn/key-pair-for-ip", aws_region="us-west-2"
+    )
+    generate_wireguard_server_configuration_file(
+        key_pairs=key_pairs,
+        server_conf_fpath=Path("/etc/wireguard/wg0.conf"),
+    )
+    generate_wireguard_server_private_key_file(
+        key_pairs=key_pairs,
+        server_key_fpath=Path("/etc/wireguard/server.key"),
+    )
+    generate_wireguard_server_public_key_file(
+        key_pairs=key_pairs,
+        server_pub_fpath=Path("/etc/wireguard/server.pub"),
+    )
+
+
+def fetch_key_pairs_from_ssm(
+    key_pairs_ssm_prefix: str,
+    aws_region: str,
+) -> List[dict]:
+    """
+    Retrieve the deserialized VPN key-pair data from ssm.
+
+    :param key_pairs_ssm_prefix: The hierarchy for the parameter, which is the parameter name except for
+        the last part of the parameter. See :py:func:``fetch_all_ssm_parameters_with_prefix``
+    :param aws_region: The AWS region where the key-pairs are stored in ssm
+    :return: The deserialized VPN key-pair data from ssm. See footski_vpn.wireguard_keygen_utils
+    """
+    key_pair_params: List[dict] = fetch_all_ssm_parameters_with_prefix(
+        path_prefix=key_pairs_ssm_prefix,
+        aws_region=aws_region,
+    )
+    key_pairs: List[dict] = deserialize_key_pair_ssm_parameters(key_pair_parameters=key_pair_params)
+
+    return key_pairs
+
+
+def generate_wireguard_server_configuration_file(
+    key_pairs: List[dict],
+    server_conf_fpath: Path = Path("/etc/wireguard/wg0.conf"),
+):
+    """
+    Generate the wireguard server configruation file.
+
+    :param key_pairs: List of key-pair data
+    :param server_conf_fpath: Path object representing the filepath to write the server configuration to
+    """
+    key_pairs_sorted_by_ip_address: List[dict] = sort_key_pairs_by_ip_address(key_pairs=key_pairs)
+
+    # generate the text for the [Interface] section
+    server_key_pair = key_pairs_sorted_by_ip_address[0]
+    interface_section = generate_wireguard_interface(server_private_key=server_key_pair["private_key"])
+
+    # generate the text for each [Peer] section
+    peer_sections = [
+        generate_wireguard_peer(
+            peer_public_key=key_pair["public_key"],
+            ip_address=key_pair["private_ip_address_on_vpn_network"],
+            owner_username=key_pair["owner_name"],
+        )
+        for key_pair in key_pairs_sorted_by_ip_address[1:]
+    ]
+
+    # combine the sections into a single string
+    sections: List[str] = [interface_section, *peer_sections]
+    server_conf_contents: str = "\n\n".join(sections)
+
+    # write the contents to the server configuration file on disk
+    server_conf_fpath.write_text(server_conf_contents, encoding="utf-8")
+
+
+def generate_wireguard_server_private_key_file(
+    key_pairs: List[dict],
+    server_key_fpath: Path = Path("/etc/wireguard/server.key"),
+):
+    """
+    Generate the wireguard server.key file.
+
+    :param key_pairs: List of key-pair data
+    :param server_conf_fpath: Path object representing the filepath to write the server.key file to
+    """
+    server_key_fpath.write_text(key_pairs[0]["private_key"], encoding="utf8")
+
+
+def generate_wireguard_server_public_key_file(
+    key_pairs: List[dict],
+    server_pub_fpath: Path = Path("/etc/wireguard/server.pub"),
+):
+    """
+    Generate the wireguard server.pub file.
+
+    :param key_pairs: List of key-pair data
+    :param server_conf_fpath: Path object representing the filepath to write the server.pub file to
+    """
+    server_pub_fpath.write_text(key_pairs[0]["public_key"], encoding="utf8")
+
+
+def generate_wireguard_interface(server_private_key: str) -> str:
+    """
+    Generate the interface for a wireguard server configuration file wg0.conf.
+
+    :param server_private_key: The private key of the wireguard VPN server
+    :return interface: A string representing the [Interface] section of the wireguard configuration file
+    """
+    interface = dedent(
+        f"""\
+    [Interface]
+    Address = 10.0.0.1/24
+    ListenPort = 51820
+    PrivateKey = {server_private_key}
+    PostUp = iptables -t nat -A POSTROUTING -o eth0 -j MASQUERADE
+    PostDown = iptables -t nat -D POSTROUTING -o eth0 -j MASQUERADE
+    """
+    )
+
+    return interface
+
+
+def generate_wireguard_peer(peer_public_key: str, ip_address: str, owner_username: str) -> str:
+    """
+    Generate a peer for a wireguard server configuration file wg0.conf.
+
+    :param peer_public_key: The public key for a peer's rsa key-pair
+    :return peer: A string representing a [Peer] section of the wireguard configuration file
+    """
+    peer = dedent(
+        f"""\
+    [Peer]
+    # Username = {owner_username}
+    PublicKey = {peer_public_key}
+    AllowedIPs = {ip_address}/32
+    """
+    )
+
+    return peer
+
+
+def fetch_all_ssm_parameters_with_prefix(path_prefix: str, aws_region: str) -> List[dict]:
+    """
+    Retrieve all key-pair aws ssm pararmters using a given prefix.
+
+    The aws parameters are retrieved using the boto3 SSM client, and the structure of the key_pair_parameters are found in the following URL.
+    https://boto3.amazonaws.com/v1/documentation/api/latest/reference/services/ssm.html#SSM.Client.get_parameters_by_path
+
+    :param path_prefix: The hierarchy for the parameter, which is the parameter name except for
+        the last part of the parameter
+    :param aws_region: The aws region where the key-pair data is stored in ssm
+    :return: The aws key-pair ssm paramters
+    """
+    # prepare an iterator to fetch the key pairs in batches
+    ssm_client = boto3.client("ssm", region_name=aws_region)
+    paginator = ssm_client.get_paginator("get_parameters_by_path")
+    response_iterator = paginator.paginate(Path=path_prefix)
+
+    # fetch all pages of parameters from SSM
+    pages: List[str, List[dict]] = [page["Parameters"] for page in response_iterator]
+    # flatten the list of lists to a single list of parameter dicts
+    parameters: List[dict] = sum(pages, [])
+
+    return parameters
+
+
+def deserialize_key_pair_ssm_parameters(key_pair_parameters: List[str]) -> List[Dict[str, str]]:
+    """
+    Deserialize the aws key-pair ssm parameters.
+
+    :param key_pair_parameters: The key-pair aws pararmeters.
+        See :py:func:``fetch_all_ssm_parameters_with_prefix``
+    :return: The VPN key-pair data. See rootski_vpn.wireguard_keygen_utils.
+    """
+    deserialized_key_pairs: List[Dict[str, str]] = [
+        json.loads(ssm_parameter["Value"]) for ssm_parameter in key_pair_parameters
+    ]
+
+    return deserialized_key_pairs
+
+
+def sort_key_pairs_by_ip_address(key_pairs: List[Dict[str, str]]) -> List[Dict[str, str]]:
+    """
+    Sort the key pairs by IP address so the keys are sequentially ordered.
+
+    :param key_pairs: The VPN key-pair data to be sorted by ip-address
+    :return sorted_key_pairs: The sorted key-pair data sequentially organized
+    """
+
+    def by_ip_address(key_pair_data: dict) -> List[int]:
+        """Return the IP address of a key pair in a form that is sortable."""
+        numerical_representation_of_ip: List[int] = [
+            int(bit) for bit in key_pair_data["private_ip_address_on_vpn_network"].split(".")
+        ]
+        return numerical_representation_of_ip
+
+    sorted_key_pairs: List[Dict[str, str]] = sorted(key_pairs, key=by_ip_address)
+    return sorted_key_pairs
+
+
+if __name__ == "__main__":
+    main()
diff --git a/infrastructure/containers/vpn/rootski_vpn/store_keys_on_aws.py b/infrastructure/containers/vpn/rootski_vpn/store_keys_on_aws.py
new file mode 100644
index 00000000..444ea398
--- /dev/null
+++ b/infrastructure/containers/vpn/rootski_vpn/store_keys_on_aws.py
@@ -0,0 +1,61 @@
+"""
+Generates a number of key-pair data and push them to AWS SSM.
+
+This file will use the file wireguard_keygen_utils.py to generate the wireguard key-pair data
+that will be pushed to aws ssm. These wireguard key-pairs will be used to set up the wireguard
+vpn running on a lightsail instance. The keys created using this script will be used by
+generate_server_conf.py
+"""
+
+import json
+from typing import Dict, List
+
+import boto3
+from mypy_boto3_ssm import SSMClient
+from wireguard_keygen_utils import generate_n_keypairs
+
+
+def store_key_pair_on_aws(key_pair_identifier: str, keypair_data: dict, ssm_client: SSMClient):
+    """
+    Store a keypair on AWS SSM.
+
+    :raises SSM.Client.exceptions.ParameterAlreadyExists: if the keypair already exists
+
+    :param key_pair_identifier: name that uniquely identifies
+        the keypair saved in parameter store. It is the last part
+        of the SSM parameter path.
+    :param keypair_data: dictionary containing the keypair data.
+        See :py:class:`wireguard_keygen_utils.VpnKeyPairData` for
+        an explanation of the contents.
+    """
+    ssm_client.put_parameter(
+        Name=f"/rootski/wireguard-vpn/key-pair-for-ip/{key_pair_identifier}",
+        Description="WireGuard Key Data",
+        Value=json.dumps(keypair_data, indent=4),
+        Type="String",
+        Overwrite=False,
+        Tier="Standard",
+        DataType="text",
+    )
+
+
+def store_n_key_pairs_on_aws(number_of_keypairs: int):
+    """Generate and store a number of keypairs on AWS SSM."""
+    ssm_client = boto3.client("ssm", region_name="us-west-2")
+
+    rootski_wireguard_keypair_data_objs: List[Dict[str, str]] = generate_n_keypairs(
+        number_of_keys=number_of_keypairs
+    )
+
+    # store all keypairs in SSM
+    for wireguard_keypaird_data in rootski_wireguard_keypair_data_objs:
+        ip_address = wireguard_keypaird_data["private_ip_address_on_vpn_network"]
+        store_key_pair_on_aws(
+            key_pair_identifier=ip_address, keypair_data=wireguard_keypaird_data, ssm_client=ssm_client
+        )
+
+
+if __name__ == "__main__":
+
+    NUMBER_OF_KEY_PAIRS_TO_GENERATE = 15
+    store_n_key_pairs_on_aws(NUMBER_OF_KEY_PAIRS_TO_GENERATE)
diff --git a/infrastructure/containers/vpn/rootski_vpn/wireguard_keygen_utils.py b/infrastructure/containers/vpn/rootski_vpn/wireguard_keygen_utils.py
new file mode 100644
index 00000000..a887e261
--- /dev/null
+++ b/infrastructure/containers/vpn/rootski_vpn/wireguard_keygen_utils.py
@@ -0,0 +1,97 @@
+"""
+Generate a number of wireguard key-pair data using the ``pywgkey`` library.
+
+See the docs: https://pywgkey.readthedocs.io/en/latest/
+We use the ``pywgkey`` library to generate wireguard keys for Rootski serverices and contributors,
+and put them into a VpnKeyPairData class. Then we will push our key-pair data to aws ssm using
+the file store_keys_on_aws.py
+"""
+from __future__ import annotations
+
+from dataclasses import dataclass
+from typing import List, Optional, Type, TypedDict
+
+from pywgkey import WgKey
+
+#: default owner of a key pair if not already assigned to a rootski contributor
+DEFAULT__VPN_IP_ADDRESS_OWNER_NAME = "unassigned"
+#: max number of IP addresses on our wireguard VPN CIDR range
+MAX_ALLOWED_WIREGUARD_KEY_PAIRS = 253
+
+
+class NumberOfKeysError(Exception):
+    """Exception for generating more keys than currently allowed."""
+
+
+class VpnKeyPairData(TypedDict):
+    """
+    Storing data for a wireguard Peer configuration.
+
+    There is an example of a peer configuration in the following documentation: https://www.wireguard.com/#cryptokey-routing
+    """
+
+    #: RSA public key for a wireguard peer
+    public_key: str
+    #: RSA private key for a wireguard peer
+    private_key: str
+    #: contributor or rootski service that reserves this IP address
+    owner_name: str
+    #: IP address on the local wireguard VPN network reserved for this peer
+    private_ip_address_on_vpn_network: str
+
+
+@dataclass
+class KeyPair:
+    """Wireguard key pair wrapper."""
+
+    public_key: str
+    private_key: str
+
+    @classmethod
+    def generate(cls: Type[KeyPair]) -> KeyPair:
+        """Generate a KeyPair object."""
+        keypair = WgKey()
+        return cls(public_key=keypair.pubkey, private_key=keypair.privkey)
+
+    def to_dict(
+        self, ip_address: str, owner_name: Optional[str] = None, note: Optional[str] = None
+    ) -> VpnKeyPairData:
+        """Convert KeyPair keys to a VpnKeyPairData dictionary object."""
+        vpn_keypair_data = VpnKeyPairData(
+            public_key=self.public_key,
+            private_key=self.private_key,
+            owner_name=owner_name or DEFAULT__VPN_IP_ADDRESS_OWNER_NAME,
+            private_ip_address_on_vpn_network=ip_address,
+            note=note,
+        )
+        return vpn_keypair_data
+
+
+def generate_n_keypairs(number_of_keys: int, num_reserved_keys: int = 10) -> List[VpnKeyPairData]:
+    """
+    Generate ``num_keys`` wireguard keypairs.
+
+    :param num_keys: number of keys to generate
+    :param num_reserved_keys: reserve certain IP addresses for rootski
+        services e.g. vpn.rootski.io, mlflow.rootski.io, etc.
+
+    :return: a list containing ``num_keys`` :py:class:`KeyPair` object
+    """
+    if number_of_keys > MAX_ALLOWED_WIREGUARD_KEY_PAIRS:
+        raise NumberOfKeysError("num_keys must be smaller than 254")
+
+    # create key pairs for IP addresses reserved for rootski services
+    reserved_key_pairs = [
+        KeyPair.generate().to_dict(
+            ip_address=f"10.0.0.{i+1}", note="This ip-address is reserved and not available for contributors."
+        )
+        for i in range(num_reserved_keys)
+    ]
+
+    # create key pairs for IP addresses assignable to rootski contributors
+    unreserved_key_pairs = [
+        KeyPair.generate().to_dict(ip_address=f"10.0.0.{i+1}") for i in range(num_reserved_keys, number_of_keys)
+    ]
+    key_pairs = reserved_key_pairs + unreserved_key_pairs
+
+    return key_pairs
diff --git a/infrastructure/containers/vpn/setup.py b/infrastructure/containers/vpn/setup.py
new file mode 100644
index 00000000..8af55aa9
--- /dev/null
+++ b/infrastructure/containers/vpn/setup.py
@@ -0,0 +1,15 @@
+"""Package definition for rootski_vpn."""
+
+import setuptools
+
+setuptools.setup(
+    name="rootski_vpn",
+    version="0.0.1",
+    description="Generate WireGuard Vpn configuration files",
+    long_description_content_type="text/markdown",
+    author="rootski-io",
+    package_dir={"": "rootski_vpn"},
+    packages=setuptools.find_packages(where="rootski_vpn"),
+    install_requires=["pywgkey==1.0.0", "boto3", "boto3-stubs[ssm]"],
+    python_requires=">=3.7",
+)