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Canary deployments of IIS using Octopus & AWS

I'm writing this more to clear my head than anything else.  If it helps someone, great.

We have measured significant 'release impact' when deploying one of our core applications.   The main problem is initialization/warmup of the appPool.  We've tried the built-in methods, but for whatever reason we are always stuck with ~25s of dead time while the first request warms things up (we assume it's warming things up, not really sure what is happening).  After that 25s wait things are very snappy and fast, so how do we prevent all of our web servers from going into 25s of dead time with production traffic inbound?

Starting point - why do this? We care about our customers, and we want to help drive our business forward with as much quality/safety/speed as possible.

Because we want to drive our business forward, we are pushing to do more and more deploys (currently we do a daily deploy, but want to see 5x that) (if you have to ask why we want 5x, readthis).  Because we ca…
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Lessons over Chinese BBQ

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Stages of product developmentProof of concept
Scope: Validating an idea, or a concept i.e. "something that's never been done before"
Ends when the idea/concept is validated or disqualified
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Should be coded as such! (i.e. hard code connection strings, because things like setting up config files is waste for this stage)

Scope: Laying the framework for your production thing.
Minimum feature set because the goal here is 'establish the product, build the foundation'.
Once the groundwork is laid, architecture set up, additional features can be added.
Should be coded as 'this will end up being production, …

Jmeter-Terraform - Dealing with AWS ELB IP changes during load testing

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Terraform applies userdata to each EC2 i…

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And I've learned a few things...

Take detailed notes of the discussion - you can use these to refresh memories, provide contrast, use for discussion points, etcTake care to note the action items, the expected outcomes, the action item owners, and update notes on this as time goes on (if you're involved with the teams)If you are doing it remotely, remember that GoToMeeting has a 6 camera limit - just because someone's face isn't on the screen doesn't mean they aren't there!  Keep everyone involved!Don't let newbies off the hook - they tend to have good insight as a relative outsiderIf a topic is voted all one colour, get people to talk about why they voted that wayTry to ensure that everyone is there, especially if the team has a track record of appreciating the time spent doing thisNote outliers/contextual changes on the results doci.e. A team recently took over a function.  Their lack of visibility into that function had previously led them to vote 'yel…

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(Will add a link to the recording here when it arrives...)
Big lessons
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Rambletron - Patterns for software development orgs?

Lessons I have learned so far; the naivete of youth allows me to write this down...the wisdom of hindsight allows future me to laugh.  :)
Building portfolio vs. delivering value This is first because it's ultimately the most important, and hardest, part to get right.
Suspect that things like this are part of it:
Business Model Generation/Value Proposition Design concepts being appliedi.e. think hard about what you are doing and whyContinuous improvement as a cultural centerpieceSenior leadership defines the big picture, explicitly calling out continuous improvement as a necessary fact of life is keyTeaching all levels to apply BMG/VPD concepts to projectsReally just the act of thinking about something vs. just doing it because you're sure it's the best idea I cannot comment on how you actually solve/execute on this, but I feel very strongly that this is core to sustainable success & innovation.
Systems thinking Books like 'Thinking in Systems' and 'The Fifth…