At first it felt like Stack Overflow on steroids.

I needed an answer → AI gave me something plausible → copy, paste, run.

A lot of what people now call “vibe coding”.

Prompt something. Accept what comes back. Fix errors as they appear. Repeat until it works.

It’s messy, but it’s also an incredible way to learn quickly.

Early on I experimented with everything I could get my hands on.

Running models locally on my Mac through Ollama. Trying different open models. Testing dev workflows.

It was interesting technically, but the development experience wasn’t great and iteration was too slow. I eventually moved fully to cloud models.

Claude and ChatGPT became the main tools.

At that stage the workflow looked something like:

prompt → generate → paste → run → debug → repeat.

I was learning UI patterns, databases, application structure — while also learning how to prompt effectively.

Back then the Claude free-tier memory limits slowed things down at times, so I bounced between Claude and ChatGPT depending on what I needed.

Eventually I actually got something running.

And I was excited.

Then the scope widened. things starting coming together for me under ArchitectFWD™ as I thought about the opportunity.

I started using AI for things outside the code:

• voiceover scripts
• AI voice tools
• image generation for socials
• content drafts

At some point this all turned into two separate products.

• prfrm — first I tested and learnt here. I focused on performance management for individuals and teams. AI-assisted goal creation, alignment and progress visibility.

• Enterprise — a platform for strategy, architecture and organisational alignment. I am super excited at how this will change outcomes for organisations who choose to join me on this journey.

Two very different problems. Two very different ways of thinking. But they’re aligned - Strategy and Execution. Structure and organisation. people, assisted by AI.

Trying to juggle both in ad-hoc AI chats stopped working pretty quickly.

Around the same time my Google Workspace renewal rolled around and I started using Gemini more heavily. That shifted things again.

Less Claude. Less ChatGPT. No more local Ollama.

The workflow became much more structured.

I started introducing:

• Product requirements documents (PRDs)
• explicit VS Code rules settings
• better context engineering
• more deliberate prompts

Most of my work now happens inside the IDE, with AI acting more like an assistant than the driver.

Gemini and ChatGPT still help with quick domain questions, explanations, and research — but the development experience and flow is much tighter.

There have definitely been mistakes along the way.

• Lost code.
• Poor commit discipline.
• Letting AI refactor too much at once.
• Learning the hard way where guardrails matter.
• Tests and migrations breaking databases

But the practices are improving.

Is it fully spec-driven development?

Not yet.

But prompts are increasingly behaving like specifications.

I’m also starting to ask for tests. Do I run them?

Is it proper TDD? Probably not.

But let’s be honest — how many teams claiming TDD actually do it well?

I am experimenting now with something closer to spec-driven development. It’s not there yet.

• Write the intent.
• Set the rules.
• Let the AI implement.
• Test
• Commit
• Ship

Sometimes the responses still need steering.

But the speed difference is remarkable.

Issue a prompt. Tell the AI to follow the rules. Lock the screen. Come back later.

It’s a pretty interesting way to build. 🚀

This is architecture, moving forward.

Architect Forward and Transform.

ArchitectFWD™ was built to close that gap.

We believe architecture isn’t documentation.

It’s direction.

Architecture is how strategy becomes real — how intent becomes coordinated action, and complexity becomes momentum.

The forward motion in FWD™ isn’t decorative. It’s deliberate.

It represents progress over perfection. Clarity over noise. Movement over stagnation.

ArchitectFWD™ isn’t a single product. It’s a structured ecosystem of advisory and platforms designed to support leaders navigating growth, scale, and transformation.

Every part of ArchitectFWD™ answers one question:

What’s the next right move — and how do we execute it well?

This is architecture, moving forward.

Architect Forward and Transform.

The architectFWD™ ecosystem as we call it is maturing and we want the branding to reflect that.

ArchitectFWD™ provides trusted strategy, architecture, and advisory expertise, expressed through a family of purpose-built platforms.

ArchitectFWD™ Enterprise is the flagship platform of the ArchitectFWD ecosystem for strategy, architecture & alignment.

Access ArchitectFWD Enterprise Platform - Software as a Service Now

ArchitectFWD™ prfrm™ is all about team and organisational performance & execution.

check out prfrm™ - by ArchitectFWD - Software as a Service

Closing thoughts

Join me in welcoming this new phase of the architectFWD strategic, transformation and advisory function increasing its reach through the architectFWD ecosystem platforms ArchitectFWD Enterprise Platform and prfrm™ - by ArchitectFWD .

The issue

This error is a known, recurring bug within the Gemini Code Assist extension for VS Code, specifically affecting users on certain operating systems or hardware configurations, including some on macOS M1/M2 chips.

The traceback shows a Go language panic (panic: runtime error: invalid memory address or nil pointer dereference), which is an internal crash within the extension’s backend process (written in Go), often triggered during the code analysis/tokenization phase (tokenizeFunc).

Since version 2.57, similar issues have been widely reported. The most reliable solution is to downgrade the extension version.

The fix

Recommended Fix: Downgrade the Extension The version you are running, v2.59.0, appears to be affected by this instability. The best immediate fix is to roll back to a known stable version.

1. Open Extensions View: In VS Code, go to the Extensions tab (Cmd+Shift+X on Mac).

2. Find the Extension: Search for Gemini Code Assist.

3. Access Downgrade Menu: Click the gear icon (⚙️) next to the extension.

4. Select Downgrade: Choose “Install Another Version…”

5. Install Stable Version: Select a version prior to 2.57.0, such as 2.56.0 or 2.55.0. These older versions are frequently cited by users as stable.

6. Disable Auto-Update: To prevent VS Code from immediately updating it again, click the gear icon (⚙️) again and select “Disable Auto Update” for the extension.

7. Restart VS Code: Completely close and reopen VS Code to ensure the downgraded version loads correctly.

Closing thoughts

I performed the downgrade and its been around 5 minutes, looks like it fixed it. Let’s wait for that new version. Right, back to getting some things done.

Zero-Downtime or Zero-Risk? Your EC2 Update Strategy

I run my services using a mix of AWS managed services and also EC2. For EC2, breaking a running stack to apply a patch is a massive failure. So, here are the two strategies to handle EC2 updates.

Option 1: The Zero-Risk Strategy (Migration)

This is the gold standard for any major OS version change, and the safest strategy for any update if your uptime requirements are near 100%. The premise is simple: We build a perfect new server, test it, and then swap the traffic.

1. Prep & Backup

Before you touch anything on the old server, create a complete recovery point.

• Create an AMI: In the EC2 Console, select your instance → Actions → Image and templates → Create Image. This is your instant, guaranteed rollback.
• Backup Data: Use scp or aws s3 sync to copy your application, data and config files to a separate location.

2. Build & Configure The New Instance

Launch a new EC2 instance using the latest Amazon Linux 2023 AMI.

• Match Settings: Use the same Instance Type, VPC, and Security Group as the old server.
• Install Packages: SSH into the new instance and install your stack:

  sudo dnf update -y
  sudo dnf install nginx certbot python3-certbot-nginx -y # and your specific packages
  

• Configure & Migrate: Copy your Nginx configuration files, Certbot files, and application code/data from the old server to the new one. Ensure file permissions are correct.

3. Testing

This step ensures the new server is flawless before the public sees it.

• Local Host File Trick: Temporarily edit your local machine’s hosts file to point your domain names to the new instance’s Public IP. Or set up new certs in ACM / certbot and routes in AWS Route 53 if preferred.
• Test Everything: Browse both your sites. Check all features, forms, and database interactions. Once satisfied, remove the entries from your hosts file.

4. Cutover (The Switch)

When you are 100% confident, update your DNS records to point the domain names to the new instance’s Public IP (or Elastic IP). Wait for the DNS TTL to expire. Traffic is now safely serving from the updated server.

You could likely make another AMI image at this point or during the process so you have it as a recovery point.

Option 2: The High-Speed Strategy (In-Place Upgrade)

If your upgrade is a minor version bump within the same OS (like AL2023.6 to AL2023.9), an in-place upgrade is faster. This is how I handle routine patching, but you must follow the safety protocol.

1. First Step (Mandatory)

Just like the migration, your AMI backup is non-negotiable.

Action: Create an AMI (Amazon Machine Image) now. Do not skip this.

2. 🔎 Risk Assessment: What Could Break

Since Nginx relies on OpenSSL and the kernel, these are your potential failure points. Breaking changes are rare in minor AL2023 updates, but they do happen via dependency bumps.

Now we update.

3. The Targeted Update

AL2023 uses versioned repositories. We need to specifically target the latest version (e.g., 2023.9.20251117) to pull all patches.

SSH in and run these commands sequentially:

# 1. Preview the changes (see which packages will be touched)
sudo dnf check-update --releasever=2023.9.20251117

# 2. Execute the upgrade command
sudo dnf upgrade --releasever=2023.9.20251117 -y

4. Final Checks And Verification

The new packages are installed, but the old kernel and services may still be running.

• Verify Nginx Config: Run this immediately after the upgrade:

  sudo nginx -t
  

• Reboot: If the kernel was updated, you must reboot.

  sudo reboot
  

• Final Check: Once back up, ensure Nginx is running and your sites are online:

  sudo systemctl status nginx
  

Closing thoughts

For major OS version changes (e.g., AL2 to AL2023), Migrate.

For minor patches within AL2023, the In-Place Upgrade is quick and efficient—as long as you have that fresh AMI backup.

Stripe

Stripe is integrated into my apps for payments and subscription plans. I also use a concept of AI credits for my apps and so those need to be refreshed for each active subscription period.

I was adding some new functionality to ArchitectFWD Enterprise (check out ArchitectFWD Enterprise Platform - Software as a Service) and so to test the AI credits and Stripe subscriptions, I started up the stripe cli listener from the command line.

FATAL Error while authenticating with Stripe: Authorization failed, status=401, body={ “error”: { “code”: “api_key_expired”, “doc_url”: “https://stripe.com/docs/error-codes/api-key-expired”, “message”: “Expired API Key provided: rk_test_*********************************….”, “type”: “invalid_request_error” } }

The fix

Log back into the Stripe dashboard and enable test mode. I’ve not yet set up the new sandbox functionality but test mode still works so I continued to set the new API keys in test mode.

Go to API Keys in the Stripe dashboard and under the standard API Keys, rotate the keys Publishable Key and Secret Key.

Then also refresh the webhook key on the Stripe developer console in the dashboard.

Go back to the command line and type

stripe config –set test_mode_pub_key pk_test_XXXXXXXX

Then the other key

stripe config –set test_mode_api_key sk_test_XXXXXXXX

These keys you should have from having performed the key rotations.

Then try start up the CLI again

stripe listen –forward-to http://localhost:8000/stripe/webhook

You should see this

Ready! You are using Stripe API Version [2024-06-20]. Your webhook signing secret is XXXXX

Set your webhook signing secret in your app and give it a test. I just created a new subscription in test mode in the Stripe dashboard.

Start up the Stripe cli -

2025-10-23 21:11:32 –> setup_intent.created [evt

looking at my logs for testing I can see

local.INFO: [StripeWebHookListener] Stripe Event setup_intent.created Payload: {“id”:”evt_…”

Looking good.

Closing thoughts

The test keys seem to have a maximum expiry length of 7 days, so get to testing and ship that feature!

AWS Bedrock

I am using AWS Bedrock and the API to embed AI in two apps I’m building currently.

When calling the API earlier I was given this error:

Error: Error executing “InvokeModel” on “https://bedrock-runtime.us-east-1.amazonaws.com/model/anthropic.claude-v2/invoke”; AWS HTTP error: Client error: POST https://bedrock-runtime.us-east-1.amazonaws.com/model/anthropic.claude-v2/invoke resulted in a 404 Not Found response: {“message”:”This model version has reached the end of its life. Please refer to the AWS documentation for more details.” (truncated…) ResourceNotFoundException (client): This model version has reached the end of its life. Please refer to the AWS documentation for more details.

Model Lifecycles

The message “This model version has reached the end of its life” indicates that the specific version of Anthropic’s Claude 2 model, identified as anthropic.claude-v2, is no longer supported or available for use on Amazon Bedrock.

This means that any applications or integrations relying on this particular model version will need to be updated to use a newer, supported Claude model. Anthropic and AWS typically provide information on model deprecations and recommended replacements.

I didnt get any notice perhaps its in the console.

Users are advised to migrate their usage to a suitable replacement model before the retirement date, as requests to deprecated models will fail after that point. For example, users who were utilizing anthropic.claude-v2 would need to migrate to a newer version like Claude 3 or Claude 4 models (e.g., Claude Sonnet 4, Claude Opus 4.1) which are available on Amazon Bedrock. Thorough testing of applications with the new models is recommended before the full transition.

Read the Bedrock model lifecycle page. It says “Amazon Bedrock is continuously working to bring the latest versions of foundation models that have better capabilities, accuracy, and safety. As we launch new model versions, you can test them with the Amazon Bedrock console or API, and migrate your applications to benefit from the latest model versions.

A model offered on Amazon Bedrock can be in one of these states: Active, Legacy, or End-of-Life (EOL)”

That link proceeds to give a information and list of active versions, legacy versions and end-of-life versions.

For legacy versions the page says “We will notify you when a model provider moves a model to the Legacy state. A model will be in the Legacy state for at least 6 months before the EOL date. While you can continue to use a Legacy model during this period, you should plan to transition to an Active model before the EOL date. New customers can’t use Legacy models and existing customers may lose access to Legacy models due to inactivity.”

For EOL models “EOL — After the EOL date, a model will be marked EOL in the console and in the following table. On, or soon after the EOL date, the model is no longer available for use in all AWS Regions and requests made to this version will fail, unless there is a private arrangement between you and the provider for continued access. You will need to migrate to the latest model by updating your application code before the EOL date. Migration will not happen automatically.”

The EOL page suggests I move to Claude Sonnet 4. I’ll do so in coming days.

Closing thoughts

As part of your governance practices you will need to be monitoring model lifecycle.

I’ve got a gap in this control and now have some migration and testing to do. I also need to figure out where the notifications on model lifecycle changes can be viewed and more reasonably subscribed to.

New feature

It is already possible to create and manage your organisation hierarchy, creating the various internal and external organisations and then these can be used later in other functions of ArchitectFWD™ Enterprise

Now the AI Assistant in ArchitectFWD™ Enterprise has been improved so that you can now generate your vision, mission, purpose and values using the organisation hierarchy and other data you capture. From a startup to a medium sized business to a large corporate, we can help with the modelling of your enterprise and your architecture.

Build your organisation and your architecture with architectFWD Enterprise. 

I’m in Builder Mode to help you architect your business, strategy, and systems.

ArchitectFWD™ Enterprise is an AI-augmented enterprise architecture platform as a service. I’m in startup mode, building this platform from the ground up with a clear vision: to empower founders, CXO, CTOs, Digital Leaders, strategists, and enterprise architects to build resilient and future-proof organizations.

Join our exclusive early access program for ArchitectFWD™ Enterprise and help us build the next generation AI-powered platform.

If you’re a founder shaping your vision, a CXO / CTO / Digital Leader driving innovation, a strategist aligning for impact, or an enterprise architect building for the future, I invite you to be part of this journey.

Sign up and be among the first to experience ArchitectFWD™ Enterprise on its available. I’m excited to build this for you.

Sign up for early access

Stay tuned for more updates as I progress through signing up as well!

Hey if your business and technology strategies are facing uncertainty and you need help, let’s connect.

Connect with me

Move your business forward with architectFWD™

#startup #advisory #strategy #technology #architecture #enterprisearchitecture #business #businessstrategy #softwareasaservice #technologystrategy #success #motivation

I’m in Founder mode. Startup mode. Dev mode. Build and Ship mode! 🎯

ArchitectFWD Enterprise Platform - Software as a Service

For those who’ve been following my blog or whom I’ve worked with in the past, you know I’m passionate about bringing clarity and strategic foresight to businessses and their technology teams through effective architecture. Today, I’m thrilled to announce the next step in that mission: ArchitectFWD™ Enterprise!

I believe there’s a better way to bridge the gap between ambitious visions and tangible results. That’s why I’ve been hard at work building an AI-augmented enterprise architecture platform designed to help you model, manage, and align your strategy, value, and technology like never before.

Unlock Strategic Clarity with AI-Powered Enterprise Architecture.

Imagine having a central hub where you can architect your entire organisation, your business strategy and the IT systems that enable it.

ArchitectFWD™ Enterprise empowers you to:

• Define your organisation and your business model and strategy with intuitive tools.
• Understand the intricate relationships between your business, value streams, and technology landscape.
• Leverage the power of AI to gain deeper insights and identify opportunities for alignment and growth.
• Make informed decisions with a holistic view of your enterprise.

Architect your business, strategy, and systems.

ArchitectFWD™ Enterprise is an AI-augmented enterprise architecture platform as a service. But I’m in Startup mode.

Yes, you read that right – I’m in startup mode, building this platform from the ground up with a clear vision: to empower founders, CXO, CTOs, Digital Leaders, strategists, and enterprise architects to build resilient and future-proof organizations.

A new way for strategic planning and execution

I’m not just building another tool; I want to be building a partnership with you in your strategic journey. ArchitectFWD™ Enterprise is designed to help evolve your business, providing intelligent insights that transform complexity into opportunity.

Unlock Strategic Clarity with AI-Powered Enterprise Architecture. Be a part of it.

ArchitectFWD™ Enterprise - an AI-augmented enterprise architecture platform to model, manage, and align strategy, value, and technology. Sign up and be part of it)

Be Among the First to Shape the Future of Enterprise Architecture.

I’m opening the doors to the exclusive early access program for ArchitectFWD™ Enterprise. This is your chance to get in on the ground floor, provide direct feedback, and help shape the next generation of AI-powered enterprise architecture. Participating helps me know that you see value in such a tool.

Join our exclusive early access program for ArchitectFWD™ Enterprise and help us build the next generation AI-powered platform.

If you’re a founder shaping your vision, a CXO / CTO / Digital Leader driving innovation, a strategist aligning for impact, or an enterprise architect building for the future, I invite you to be part of this journey.

Sign up and be among the first to experience ArchitectFWD™ Enterprise on its available. I’m excited to build this for you.

Sign up for early access

Stay tuned for more updates as I progress through signing up as well!

Lastly, if your business needs strategic tech guidance but not a full-time hire, let’s connect.

Connect with me

Move your business forward with architectFWD™

#startup #advisory #strategy #technology #architecture #enterprisearchitecture #business #businessstrategy #softwareasaservice #technologystrategy #success #motivation

What is a Fractional CTO / Enterprise Architect?

💡 What is a Fractional CTO / Enterprise Architect (EA)?

Not every company needs a full-time CTO or EA, but many need their expertise. A fractional role means:

✅ You get on-demand leadership & guidance

✅ You pay only for what you need (flexible engagement)

✅ You gain senior-level strategic insight without long-term overhead

Startups, scale-ups, and even enterprises can accelerate growth, avoid costly mistakes, and optimize their tech stack with fractional support.

Would a fractional tech leader make sense for your business? Let’s discuss!

When would your business need a fractional CTO / Enterprise Architect

These are good signs -

• There is uncertainty about how to realise strategic aspirations.

• Your business is struggling with technology, scaling, and architecture decisions.

• Your engineering and technical teams need some targetted advice or mentoring.

That’s the best time to engage with me, to make use of ArchitectFWD services in strategy, transformation and advisory.

What would I do as in this fractional CTO / Enterprise Architect role?

It depends. Who doesn’t love that answer. Seriously though, it depends on what you need, but ultimately it is about understanding your business and setting a strategy that helps to meet and exceed your business goals.

If your business needs strategic tech guidance but not a full-time hire, let’s connect!

#FractionalCTO #EnterpriseArchitecture #ScalingTech

Connect with me

Move your business forward with architectFWD™

26/05/2025 - Edited date of post which was incorrectly set.