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End to End Security &
Operations with Chainguard
& Weave GitOps
Trust & validation for builds & configuration
In partnership with:
2
2
Webinar Platform - FAQs
Using Zoom
• You are in listen only mode
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submit questions
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Technical Issues - please visit Zoom Help
https://support.zoom.us/hc/en-us/articles/206175806-Top-Questions
3
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James Strong
Solutions Architect
Chainguard
James joined Chainguard after a long stint of helping
customers migrate to the Cloud and Kubernetes.
Security was the number one issue he saw when
completing these migrations, and he now wants to help
secure their supply chains. James is also co-authors of
O’Reilly’s Networking & Kubernetes, KubePhilly meetup
organizer, and ACloud Guru instructor on Advanced
Networking With Kubernetes For AWS. You can find him
in the gym doing Olympic weightlifting or playing Rugby
when he is not at a computer.
Leo Murillo
Principal Solutions Architect
Weaveworks
Leo brings wide-ranging industry perspective, with
over 20 years of experience building technology and
leading teams all the way from Startups to Fortune
500s. He is passionate about cloud native
technologies, organizational transformation and the
open source community. As Principal Partner
Solutions Architect at Weaveworks, he focuses on
helping solve application and infrastructure delivery
challenges on Kubernetes at scale.
Speaker introductions
4
Confidential do not distribute 4
- Software Supply Chain Security
- Identity and Trust
- Chainguard Enforce for Git
- Weave GitOps Enterprise
- Securing Build and Configuration Demo!
Agenda for today
5
Software Supply Chain
Security
Chainguard | Make your software supply chain secure by default
1 2 3 4
Source Code Dependencies
Build
Pipelines
Artifacts Deployments
5
A software supply chain is the series of steps performed when writing, testing,
packaging, and distributing application software to end consumers.
Software supply chain
7
Identity and Trust
● On the Internet, nobody knows
you're a dog.
● How do you prove you are who you
say you are?
Identity
Attacks in the wild
9
# Sign a commit
$ git commit -S
# Verify commit
$ git verify-commit <rev>
How to sign Git commits - tl;dr
Git Config Options
● commit.gpgSign - sign all commits
● commit.tagSign - sign all tags
● user.signingKey - key to use for signing
● gpg.format - key format (gpg, x509, ssh)
● gpg.<format>.program - program to use to
sign (must be on path)
● + more depending on the tool
$ git cat-file commit HEAD
tree 7dd968bb81c8eaa2e9cbaaa872ba93eba0d46b3a <- Where are the files
parent 883166b86e62178d1c40eb646675c38bc83a5b0b <- What's the last commit(s)
author James Strong <james.strong@chainguard.dev> 1650465912 -0400 <- Who made the change
committer James Strong <james.strong@chainguard.dev> 1651877196 -0400 <- Who applied it to the repo
Fix the thing with the stuff <- Commit message
gpgsig -----BEGIN SIGNED MESSAGE-----
MIIDawYJKoZIhvcNAQcCoIIDXDCCA1gCAQExDTALBglghkgBZQMEAgEwCwYJKoZI
hvcNAQcBoIICGDCCAhQwggGboAMCAQICFADE86Sdbdy3wusCpdgYNg3GaMiHMAoG
CCqGSM49BAMDMCoxFTATBgNVBAoTDHNpZ3N0b3JlLmRldjERMA8GA1UEAxMIc2ln
-----END SIGNED MESSAGE-----
Signed commit
What's in a signed commit
Challenges with
traditional signing
● Encryption?
● Rotation?
● Stored in a well known location
● Compromise Detection
● Revocation
"I have a pretty decent security setup… but GPG is
such a usability nightmare I don't want to touch it
with a 10 foot pole."
- on HN
13
Gitsign – Keyless Git
Commit Signing
● Easy: free users from key
management
● Meet developers where they
are
○ Support GPG keys, hardware
tokens
● Accept centralization
○ With accountability (like web PKI)
● Integrate with other tools
○ Software supply chain solutions
○ Developer tools and infrastructure
Sigstore Goals
● “A new kind of CA”
● Users authenticate
○ OpenID Connect (OIDC ==
“login with Google”)
● Issues X.509 code signing
certificate
○ SubjectAlternativeName:
“James Google account”
○ Ephemeral (10 minute validity)
Identity
● Certificate lifetime:
○ Short-lived? Pain: frequent
re-signing.
○ Long-lived? Risky!
● Sign while cert valid; verify later.
○ Separate signature and cert
lifetime
● Rekor: attest to timestamp!
○ Like timestamp authority (TSA)
○ Extra metadata, searchable
Identity
Sigstore Adoption
What if…
Enter Gitsign!
Chainguard | Make your software supply chain secure by default
Enforce for Git
Chainguard | Make your software supply chain secure by default
Powered by
Signing git commits Enforcement
https://github.com/apps/chainguard-enforce
No key management
Easy to configure
Just works
git config --local commit.gpgsign true
git config --local tag.gpgsign true
git config --local gpg.x509.program gitsign
git config --local gpg.format x509
https://github.com/sigstore/gitsign
Chainguard | Make your software supply chain secure by default
Developer Use
CSM CI/CD Distribution
Source
Dependency
Build Package
Solution
Enforce for Git Cosign
Github Actions
23
Confidential do not distribute 23
Now, let’s look into Weave GitOps
24
Confidential do not distribute 24
A Kubernetes Native Platform for delivery, policy
and lifecycle management of clusters and cloud
native applications applying the GitOps
Operating Model
What is Weave GitOps?
25
Confidential do not distribute 25
Let’s talk real quick about GitOps and the
Weave GitOps Architecture
2
6
Weave GitOps OSS (for Apps)
● App platform + addons
● App dev tools (GUI, IDE)
● App delivery (CICD)
Accelerator Catalog:
Commercial Software
AcceleratorTemplates
Assured Tier
+ Enterprise Flux
+ Assured OSS Builds
+ Weave Certified OSS
Multi-tenant
Workspaces
App
Management
Platform
Accelerator Catalog:
Verified Profiles etc
Multi- Cluster
Manager
Trusted
Delivery
Mixed
Clusters
B/Metal
Accelerator Catalog: Curated addons and supported integrations for
3rd
party vendors eg Terraform Enterprise Edition
Weave GitOps Versions
App platform + addons
● App dev tools (GUI, IDE)
● App delivery (CICD)
Accelerator Catalog:
Commercial Software
Solution Templates
Suite of Open Source tools
Enterprise Flux & Flagger
+ Assured OSS Builds
+ Weave Certified OSS
Accelerator Catalog:
Verified Profiles
Bitstream, Hotfix
Support SLAs + CVEs
Flux and Flagger: Open Source CNCF projects
Weave GitOps OSS: Open Source Flux Extension + GUI
Weave GitOps OSS
Open Source Software with Community Support
Weave GitOps Assured
Open Source Software with Enterprise Support
Weave GitOps Enterprise
Open and Closed Source Software with Enterprise Support
27
Confidential do not distribute 27
● Is Modular: Use the parts of the platform you need.
● Is Secure: Utilizing repository authorization and Kubernetes authorization, Weave GitOps Enterprise doesn’t
require additional authorization configurations to be secure.
● Utilizes the Best of Weaveworks Open Source: Our tools and methodology is the basis for Weave GitOps
Enterprise.
● Is Supported: Not only the Weave GitOps Enterprise tools, but Kubernetes and the surrounding
components as well.
● Is GitOps Top to Bottom: Everything we build uses the GitOps methodology.
Weave GitOps OSS & Enterprise
28
App
Team
workspaces
App
Management Cluster
App
Leaf Cluster
Profile Policy
Management
Management
UI
Weave GitOps Enterprise
Kubernetes
Cluster Management UI
Management UI
Multi Cluster Installer (CAPI)
Weave GitOps Enterprise
Kubernetes
29
29
Desired State
Store all code and
configuration
Actual State
Runtime
environment
Automation
Single interface
to operations
App
Runtime Env
App
3
0
Revert Any change
● Any change to the system will diverge the
‘desired state’ from the actual state
● We can always return to our previous known
good value - every change is automic
kubectl apply
Prod Cluster
Automatic or Manual
Response App App
31
Manual
Approval
Repository
Move fast and don’t break things
● Represents the entire state of the system - platform, services
and applications
● We can easily inspect changes ensuring they meet standards
● We can over-ride and put in guard rails to protect the system
● Revert changes to return to an earlier known good state
Control
Locked
parts
Alert
Pull
Request
Inspect
Audit Manage
App
Prod Cluster
App
32
Confidential do not distribute 32
DEMO
33
33
Q&A
(Please use the Q&A panel to submit a question)
34
34
Whitepaper: Trusted Application Delivery
https://bit.ly/3A0JMOe
Learn more about Weave GitOps
www.weave.works/enterprise and a 5 min demo
https://youtu.be/aqJaHNCz2lM
Request a personal demo
www.weave.works/contact
Thank You
Thank You
chainguard.dev/assessment
Where are you in your software supply chain journey?
Chainguard will audit your software supply chain and
deliver concrete steps you can take to fix security gaps.
Supply Chain Assessment
James Strong
james.strong@chainguard.dev
chainguard.dev/newsletter
Stay up to date on software supply chain security
happenings and news from the open source community,
and get sneak peeks at what the Chainguard team is up to.
Subscribe to Chainmail
chainguard.dev/contact
Contact the team!

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Webinar: End to End Security & Operations with Chainguard and Weave GitOps

  • 1. 1 1 End to End Security & Operations with Chainguard & Weave GitOps Trust & validation for builds & configuration In partnership with:
  • 2. 2 2 Webinar Platform - FAQs Using Zoom • You are in listen only mode • This webinar is being recorded • Q&A session will follow the presentation, please use the Q&A panel to submit questions • Hit escape to exit full screen • Slides and recording will be shared after the webinar Technical Issues - please visit Zoom Help https://support.zoom.us/hc/en-us/articles/206175806-Top-Questions
  • 3. 3 3 James Strong Solutions Architect Chainguard James joined Chainguard after a long stint of helping customers migrate to the Cloud and Kubernetes. Security was the number one issue he saw when completing these migrations, and he now wants to help secure their supply chains. James is also co-authors of O’Reilly’s Networking & Kubernetes, KubePhilly meetup organizer, and ACloud Guru instructor on Advanced Networking With Kubernetes For AWS. You can find him in the gym doing Olympic weightlifting or playing Rugby when he is not at a computer. Leo Murillo Principal Solutions Architect Weaveworks Leo brings wide-ranging industry perspective, with over 20 years of experience building technology and leading teams all the way from Startups to Fortune 500s. He is passionate about cloud native technologies, organizational transformation and the open source community. As Principal Partner Solutions Architect at Weaveworks, he focuses on helping solve application and infrastructure delivery challenges on Kubernetes at scale. Speaker introductions
  • 4. 4 Confidential do not distribute 4 - Software Supply Chain Security - Identity and Trust - Chainguard Enforce for Git - Weave GitOps Enterprise - Securing Build and Configuration Demo! Agenda for today
  • 6. Chainguard | Make your software supply chain secure by default 1 2 3 4 Source Code Dependencies Build Pipelines Artifacts Deployments 5 A software supply chain is the series of steps performed when writing, testing, packaging, and distributing application software to end consumers. Software supply chain
  • 8. ● On the Internet, nobody knows you're a dog. ● How do you prove you are who you say you are? Identity
  • 9. Attacks in the wild 9
  • 10. # Sign a commit $ git commit -S # Verify commit $ git verify-commit <rev> How to sign Git commits - tl;dr Git Config Options ● commit.gpgSign - sign all commits ● commit.tagSign - sign all tags ● user.signingKey - key to use for signing ● gpg.format - key format (gpg, x509, ssh) ● gpg.<format>.program - program to use to sign (must be on path) ● + more depending on the tool
  • 11. $ git cat-file commit HEAD tree 7dd968bb81c8eaa2e9cbaaa872ba93eba0d46b3a <- Where are the files parent 883166b86e62178d1c40eb646675c38bc83a5b0b <- What's the last commit(s) author James Strong <james.strong@chainguard.dev> 1650465912 -0400 <- Who made the change committer James Strong <james.strong@chainguard.dev> 1651877196 -0400 <- Who applied it to the repo Fix the thing with the stuff <- Commit message gpgsig -----BEGIN SIGNED MESSAGE----- MIIDawYJKoZIhvcNAQcCoIIDXDCCA1gCAQExDTALBglghkgBZQMEAgEwCwYJKoZI hvcNAQcBoIICGDCCAhQwggGboAMCAQICFADE86Sdbdy3wusCpdgYNg3GaMiHMAoG CCqGSM49BAMDMCoxFTATBgNVBAoTDHNpZ3N0b3JlLmRldjERMA8GA1UEAxMIc2ln -----END SIGNED MESSAGE----- Signed commit What's in a signed commit
  • 12. Challenges with traditional signing ● Encryption? ● Rotation? ● Stored in a well known location ● Compromise Detection ● Revocation "I have a pretty decent security setup… but GPG is such a usability nightmare I don't want to touch it with a 10 foot pole." - on HN
  • 13. 13 Gitsign – Keyless Git Commit Signing
  • 14. ● Easy: free users from key management ● Meet developers where they are ○ Support GPG keys, hardware tokens ● Accept centralization ○ With accountability (like web PKI) ● Integrate with other tools ○ Software supply chain solutions ○ Developer tools and infrastructure Sigstore Goals
  • 15. ● “A new kind of CA” ● Users authenticate ○ OpenID Connect (OIDC == “login with Google”) ● Issues X.509 code signing certificate ○ SubjectAlternativeName: “James Google account” ○ Ephemeral (10 minute validity) Identity
  • 16. ● Certificate lifetime: ○ Short-lived? Pain: frequent re-signing. ○ Long-lived? Risky! ● Sign while cert valid; verify later. ○ Separate signature and cert lifetime ● Rekor: attest to timestamp! ○ Like timestamp authority (TSA) ○ Extra metadata, searchable Identity
  • 20. Chainguard | Make your software supply chain secure by default Enforce for Git
  • 21. Chainguard | Make your software supply chain secure by default Powered by Signing git commits Enforcement https://github.com/apps/chainguard-enforce No key management Easy to configure Just works git config --local commit.gpgsign true git config --local tag.gpgsign true git config --local gpg.x509.program gitsign git config --local gpg.format x509 https://github.com/sigstore/gitsign
  • 22. Chainguard | Make your software supply chain secure by default Developer Use CSM CI/CD Distribution Source Dependency Build Package Solution Enforce for Git Cosign Github Actions
  • 23. 23 Confidential do not distribute 23 Now, let’s look into Weave GitOps
  • 24. 24 Confidential do not distribute 24 A Kubernetes Native Platform for delivery, policy and lifecycle management of clusters and cloud native applications applying the GitOps Operating Model What is Weave GitOps?
  • 25. 25 Confidential do not distribute 25 Let’s talk real quick about GitOps and the Weave GitOps Architecture
  • 26. 2 6 Weave GitOps OSS (for Apps) ● App platform + addons ● App dev tools (GUI, IDE) ● App delivery (CICD) Accelerator Catalog: Commercial Software AcceleratorTemplates Assured Tier + Enterprise Flux + Assured OSS Builds + Weave Certified OSS Multi-tenant Workspaces App Management Platform Accelerator Catalog: Verified Profiles etc Multi- Cluster Manager Trusted Delivery Mixed Clusters B/Metal Accelerator Catalog: Curated addons and supported integrations for 3rd party vendors eg Terraform Enterprise Edition Weave GitOps Versions App platform + addons ● App dev tools (GUI, IDE) ● App delivery (CICD) Accelerator Catalog: Commercial Software Solution Templates Suite of Open Source tools Enterprise Flux & Flagger + Assured OSS Builds + Weave Certified OSS Accelerator Catalog: Verified Profiles Bitstream, Hotfix Support SLAs + CVEs Flux and Flagger: Open Source CNCF projects Weave GitOps OSS: Open Source Flux Extension + GUI Weave GitOps OSS Open Source Software with Community Support Weave GitOps Assured Open Source Software with Enterprise Support Weave GitOps Enterprise Open and Closed Source Software with Enterprise Support
  • 27. 27 Confidential do not distribute 27 ● Is Modular: Use the parts of the platform you need. ● Is Secure: Utilizing repository authorization and Kubernetes authorization, Weave GitOps Enterprise doesn’t require additional authorization configurations to be secure. ● Utilizes the Best of Weaveworks Open Source: Our tools and methodology is the basis for Weave GitOps Enterprise. ● Is Supported: Not only the Weave GitOps Enterprise tools, but Kubernetes and the surrounding components as well. ● Is GitOps Top to Bottom: Everything we build uses the GitOps methodology. Weave GitOps OSS & Enterprise
  • 28. 28 App Team workspaces App Management Cluster App Leaf Cluster Profile Policy Management Management UI Weave GitOps Enterprise Kubernetes Cluster Management UI Management UI Multi Cluster Installer (CAPI) Weave GitOps Enterprise Kubernetes
  • 29. 29 29 Desired State Store all code and configuration Actual State Runtime environment Automation Single interface to operations App Runtime Env App
  • 30. 3 0 Revert Any change ● Any change to the system will diverge the ‘desired state’ from the actual state ● We can always return to our previous known good value - every change is automic kubectl apply Prod Cluster Automatic or Manual Response App App
  • 31. 31 Manual Approval Repository Move fast and don’t break things ● Represents the entire state of the system - platform, services and applications ● We can easily inspect changes ensuring they meet standards ● We can over-ride and put in guard rails to protect the system ● Revert changes to return to an earlier known good state Control Locked parts Alert Pull Request Inspect Audit Manage App Prod Cluster App
  • 32. 32 Confidential do not distribute 32 DEMO
  • 33. 33 33 Q&A (Please use the Q&A panel to submit a question)
  • 34. 34 34 Whitepaper: Trusted Application Delivery https://bit.ly/3A0JMOe Learn more about Weave GitOps www.weave.works/enterprise and a 5 min demo https://youtu.be/aqJaHNCz2lM Request a personal demo www.weave.works/contact Thank You
  • 35. Thank You chainguard.dev/assessment Where are you in your software supply chain journey? Chainguard will audit your software supply chain and deliver concrete steps you can take to fix security gaps. Supply Chain Assessment James Strong james.strong@chainguard.dev chainguard.dev/newsletter Stay up to date on software supply chain security happenings and news from the open source community, and get sneak peeks at what the Chainguard team is up to. Subscribe to Chainmail chainguard.dev/contact Contact the team!