Configure SSH on Windows 10 | Configure SSH Server | Free SSH Server
SSH Product Overview - Venafi · PDF fileSSH Product Overview ... No key rotation ... Lab:...
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SSH Product Overview
SSH Product Overview
▪ Understanding SSH
▪ SSH Discovery and Remediation
▪ Agentless SSH
▪ Agent Based SSH
Where is SSH used?
SSHTLS
Customers
Partners
EmployeesAdmins with Root Access
ApplicationOwners
SystemAdmins
SSH (SCP or SFTP)
File Transfer & Remote Script
Execution
Jupiter
Where is SSH used?
SSHTLS
Customers
Partners
EmployeesAdmins with Root Access
ApplicationOwners
SystemAdmins
SSH (SCP or SFTP)
File Transfer & Remote Script
Execution
Jupiter
Simple rule of thumb:
If it’s not Windows or a Mainframe, SSH is
probably used to login into it.
SSH Basics – User Access
Host Keys
Server11
User Keys
AHost Keys
Server11
Server Keys
1
Server1
Server2
Alice
Server Keys
1Authorized Keys
AliceA Server Keys
2Authorized Keys
AliceA
User Keys
AHost Keys
Server11
Server22
SSH Basics – Server-to-Server Access
Trusted Keys
Server11
Client Keys
C
Trusted Keys
Server11
Server1
Server2
Alice
Server Keys
1Authorized Keys
AliceA Server Keys
2Authorized Keys
AliceA
User Keys
AHost Keys
Server11
Server22
Server Keys
1Authorized Keys
AliceA
Server22
Server Keys
2User Keys
2Authorized Keys
AliceAHost Keys
Server11
The State of SSH in Most Organizations
▪ No inventory
▪ No key rotation
▪ Weak keys
▪ Terminated employees still have access
▪ Potential backdoor keys
▪ Pivoting opportunities for attackers
SSH Discovery and Remediation
Venafi Products can discover and report back to Venafi server crucial details about SSH keys.
Discovery is a critical part of identifying the status of your SSH key environment across all of your systems.
SSH Discovery and Remediation
Identifying orphaned public keys and resolving them quickly can help to avoid potentially serious vulnerabilities, particularly when an orphaned key is found in a root or administrative account on a server.
Venafi Products allow us to add/remove SSH keys.
Agentless SSH
▪ TPP server(s) will SSH to target systems to perform scans and remediation
▪ Work performed at the time of User UI action
▪ Discussed in detail in it’s own module
Agent Based SSH
▪ Requires installation of Agent software
▪ Supports wide range of OS types
▪ Can gather SSH Key Usage info
▪ Agents call home for work
▪ Discussed in detail in it’s own module
Agent vs. Agentless Considerations
▪ Network traffic direction
▪ Agent(+): Key usage logging
▪ Agentless(+): More platform independent (e.g., mainframe, etc.)
▪ Agentless(-): Credential management for our own agentless access
▪ Agent(+): Better support for “intermittent” systems (e.g., user laptops)
▪ Agent(+): Support for Windows
Review
1. What are SSH Keys used for?
2. What is the purpose of authorized_keys file?
3. What is default expiration for a SSH key?
Agentless SSH
Agentless SSH Overview
▪ SSH discovery can find SSH keys on devices that do not have agents installed on them
▪ SSH Remediation can add and remove SSH keys
▪ TPP uses a remote SSH connection to connect to the systems or servers
▪ TPP will scan per configured work and create keysets in Aperture
Configuring Agentless SSH
▪ Create Credential Objects
▪ Create Device Objects
▪ Configure SSH Work
▪ Allow scheduled work to happen
▪ View Results in Aperture
Create Credential Objects
▪ Password (Aperture or WebAdmin)
▪ SSH Private Key (WebAdmin)
Create Device Objects
▪ Done in WebAdmin
▪ Supports sudo
▪ Set Temp Directory if using sudo
Device Objects
▪ Device Inventory▪ See status of Devices▪ Use filters▪ Can be created using Network Discovery
View Device Objects
▪ Shows status info
▪ Test Connection
Edit Device Objects
Configure Agentless SSH Work
▪ Enable folders for Agentless
Configure Agentless SSH Work
▪ Create Group
▪ Agent Type = No Agent Installed
Configure Agentless SSH Work
▪ Hardcodes Membership Criteria
Configure Agentless SSH Work
▪ Work Types:
‐ SSH Discovery
‐ SSH Remediation
▪ Work explained in upcoming module
Run Agentless SSH Scan
▪ Runs per schedule
▪ Can be triggered on demand
Lab: Agentless SSH
▪ Lab coming up after next module
Review
1. What are benefits of Agentless SSH?
2. Can we mix and match Agent and Agentless SSH?
3. Can Agentless SSH typically be used with Windows Servers?
Configuring SSH Work
Configuring SSH Work Overview
▪ SSH work can apply to Agents and Agentless SSH
▪ Done on the Group under Agents > Groups
▪ Specify what to scan
▪ Specify where to scan
▪ Specify when to scan
▪ Enable Remediation
Enabling SSH Discovery Work
▪ We can create a new group for SSH work only
▪ Discover SSH Work = Yes
SSH Discovery Work Settings
▪ Scan interval is similar to Agent check-in time options are:
‐ Daily
‐ Weekly
‐ Monthly
‐ Hourly
‐ On Receipt
‐ Every 30 Minutes
▪ Randomization to not over load VMs
SSH Discovery Work Settings
Default scan paths for SSH server information and keys.
SSH Discovery Work Settings
▪ Specify folder where agent will look for:‐ Host Keys
‐ User Keys
‐ Host Keys and User Keys
▪ Supports wildcards
▪ Specify where to not scan
SSH Discovery Work Settings
▪ Should the agent scan Network File System (NFS) mount points
▪ Minimize the impact of discovery
SSH Discovery Work Settings
▪ Select a file size threshold after which the agent should ignore files
▪ By setting this limit to 1mb, all keystore files larger than 1mb are ignored during SSH discovery.
SSH Discovery Work Settings
▪ Logging level detail
▪ Default is Info
▪ Written to System logs
SSH Remediation Work
▪ SSH Remediation > Remediate SSH Work = Yes
SSH Remediation Work
▪ How often Agents check for Remediation work
▪ Interval between Monthly and 1min
▪ Randomization▪ Start time▪ Agentless SSH
performs work immediately
SSH Remediation Work
▪ Logging level detail
▪ Default is Info
▪ Agent Writes to:
‐ Syslog
‐ Event Logs
SSH Key Usage Work
▪ SSH Key Usage > Collect SSH Logs = Yes
SSH Key Usage Work
▪ How often Agents Deliver SSH Key Usage data
▪ Interval between daily and 1min
▪ Randomization
SSH Key Usage Work
▪ Cache size on Agent side
▪ Agent logging for SSH Key Usage
SSH Key Usage – Agent side
▪ Only Venafi Agent can gather SSH Key Usage!
▪ Steps required on Venafi Agent side:
https://support.venafi.com/hc/en-us/articles/215911487
Lab: Configuring SSH Work
SSH labs can be done with Agentless or Agent Based SSH.
▪ Configuring Agent SSH Work Lab
‐ Agent SSH configuration
‐ Enable Discovery and Remediation
▪ Configuring Agentless SSH Lab
‐ Agentless Based SSH configuration
‐ Enable Discovery and Remediation
Review
1. Where are SSH Discovery results placed?
2. How often will the Agents scan for SSH Keys?
3. How often will Agentless SSH scan run?
4. Where does the Agent log SSH discovery information?
Creating and Configuring
SSH Policy
Working with SSH Key Policies
▪ Lock or suggest values*
▪ Settings inherited down the tree
▪ Agents represented in Policy structure
▪ Permission assignment
▪ Find policy violations
*Unlike Certificate Policy, some locked values are just for reporting. For example multiple private key instances when locked to not allowed.
Configuring SSH Policy
▪ Done in Aperture
▪ Configuration > Policies
▪ Opens Policy tree view
▪ Click on folder icon to expand
SSH Policy - General
SSH Policy - General
SSH Policy - General
SSH Policy - General
▪ Let's you allow or deny user access to one or more remote IP addresses or host names
▪ Setting will be added to authorized_keys
SSH Policy - General
▪ Using forced commands, you can limit user accounts SSH access and usage
▪ Instead of the client's deciding which command will run, the Policy forces the command
SSH Policy - General
▪ Login options in authorized_keys for example:
‐ no-user-rc
‐ no-X11-forwarding
‐ no-agent-forwarding
▪ More found in documentation
SSH Policy – Device Connection
Dashboard
Dashboard
SSH Keysets
▪ Inventory > SSH Keys
Orphan keys
▪ SSH Keys > Orphans
▪ Shows keysets where we don’t know about the matching private or public key
▪ We can see that some one has root access to multiple systems
Keyset details
Keyset details
Host Trust Map
Devices
▪ Inventory > Devices
▪ View Device status, no need to check each keyset separately
Looking at a Device
▪ Overview▪ SSH Client info▪ SSH Host info▪ Permissions
SSH Client – Outgoing Access
▪ Shows client keyset instances on this host▪ Show a warning when something is out of compliance
SSH Client – Known Host Keys
▪ Shows discovered known_hosts keys
SSH Server – Authorized Clients
▪ Shows keys that grant access to the system
SSH Server – Host Keysets
▪ Shows Host Keysets
Lab: SSH Policy Lab
▪ Configure Policies for SSH
▪ View SSH Key Discovery results
Review
1. What can we do through SSH Policy?
2. Can SSH Policy be configured through WebAdmin?
3. What is Host Trust Map?
4. What is the difference between SSH Host and Client keyset?
Responding to SSH Key Threats
SSH Remediation
SSH Remediation
In order to prevent lateral attacks on your critical servers and related network resources, you must be able to find, identify, organize, and renew your SSH key assets.
Remediation allows us to rotate existing keys and provision new ones.
Enable Remediation
▪ Configuration > Folders
▪ Only available through Policy (not on specific keyset)
Remediation Enabled – Private Keys
Remediation Enabled – Auth Keys
Working with Keysets
▪ Inventory > SSH Keys
▪ Create New Keyset
Creating New Keysets
Creating New Keysets
Adding Key Instances
▪ Adding a Public Key instance to a Keyset
▪ Adding a Private Key instance to a Keyset
Removing Key Instances
▪ Removing a key instance
Add Public Key instance
Making changes to Key instances
▪ Editing a Public key instance
Making changes to Key instances
▪ Make changes and click Save
Rotating Keys
▪ Start key rotation
Rotating Keys
▪ Host Key rotation will pause and go into a “Reconfigure” stage
▪ Chance to manually restart/reconfigure SSHd if needed
Changes To Keys Outside TPP
Detect
Remediate
Remote Add:
Remote Delete:
Remote Edit:
- Detect: Add to TPP
- Detect: Delete from TPP
- Detect: Edit in TPP
- Remediate: Add to TPP
- Remediate: Restore on remote
- Remediate: Restore on remote
Resolving common violations
▪ Resolving Orphans
▪ Track the status of Orphan Keys
▪ Resolving Duplicate Private Keys
▪ Old Keys
▪ Weak Keys
Resolving Orphans
▪ Mapping to an External Key‐ No corresponding private key instance
‐ Creates proxy of the private key
▪ Deleting Orphans‐ Would allow administrator or root access to system
‐ Cannot discover or verify the owner of a key
‐ Use Mark As feature if not 100% sure
Tracking the status of orphans
▪ To keep track of the work we have done with each keyset, we can use the Mark As option
▪ Mark As lets us set the status of each keyset to either Reviewed As OK or Reviewed Needs Action
▪ Lets you identify which keysets have already been reviewed
Mark As
▪ Reviewed As OK‐ Indicates that you have already resolved an orphan
▪ Reviewed Needs Action‐ Unauthorized User Trust‐ Rogue‐ Suspect‐ Owned by Former Employee
▪ Generates an event
Resolving Duplicate Private Keys
▪ Compliant duplicate keys
‐ No needed
▪ Non-compliant
‐ Remove non-compliant instances
Resolving Accessible Root Accounts
▪ Root accounts at the server level are typically to be avoided or kept to a minimum
‐ Remove Public Key instance from authorized_keys
‐ Add a User-access only public key
Weak Key Lenghts
▪ Small key length keys introduce risk
‐ Rotate keys to comply with policy, typically to RSA 2048 or DSA 1024 keys (suggested minimum sizes per algorithm)
Resolving Old Keys
▪ Keys older than allowed by Policy
‐ Rotate keys
‐ Remove keys
Lab: SSH Remediation Lab
▪ Reviewing a keyset and mark as External key access
▪ Rotate a Private Key
▪ Remove a Key instance
▪ Provision a new Keyset to grant alice access from ServerA to ServerB
Review
1. Why would you create a new Keyset?
2. Can you set SSH keys to auto-renew?
3. Can keys be downloaded from Aperture?
4. Can you upload a SSH Private Key to Aperture?
Course Review
VSP16 Course Review
Test Preparation
▪ Question & Answer
▪ Take Test
▪ Open Book
▪ Timed
▪ Test is at https://training.venafi.com
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