diff --git a/docs/README.skills.md b/docs/README.skills.md
index b327a06cd..aac5f9b55 100644
--- a/docs/README.skills.md
+++ b/docs/README.skills.md
@@ -68,7 +68,7 @@ See [CONTRIBUTING.md](../CONTRIBUTING.md#adding-skills) for guidelines on how to
 | [az-cost-optimize](../skills/az-cost-optimize/SKILL.md)<br />`gh skills install github/awesome-copilot az-cost-optimize` | Analyze Azure resources used in the app (IaC files and/or resources in a target rg) and optimize costs - creating GitHub issues for identified optimizations. | None |
 | [azure-architecture-autopilot](../skills/azure-architecture-autopilot/SKILL.md)<br />`gh skills install github/awesome-copilot azure-architecture-autopilot` | Design Azure infrastructure using natural language, or analyze existing Azure resources to auto-generate architecture diagrams, refine them through conversation, and deploy with Bicep.<br />When to use this skill: - "Create X on Azure", "Set up a RAG architecture" (new design) - "Analyze my current Azure infrastructure", "Draw a diagram for rg-xxx" (existing analysis) - "Foundry is slow", "I want to reduce costs", "Strengthen security" (natural language modification) - Azure resource deployment, Bicep template generation, IaC code generation - Microsoft Foundry, AI Search, OpenAI, Fabric, ADLS Gen2, Databricks, and all Azure services | `.gitignore`<br />`assets/06-architecture-diagram.png`<br />`assets/07-azure-portal-resources.png`<br />`assets/08-deployment-succeeded.png`<br />`references/ai-data.md`<br />`references/architecture-guidance-sources.md`<br />`references/azure-common-patterns.md`<br />`references/azure-dynamic-sources.md`<br />`references/bicep-generator.md`<br />`references/bicep-reviewer.md`<br />`references/phase0-scanner.md`<br />`references/phase1-advisor.md`<br />`references/phase4-deployer.md`<br />`references/service-gotchas.md`<br />`scripts/cli.py`<br />`scripts/generator.py`<br />`scripts/icons.py` |
 | [azure-deployment-preflight](../skills/azure-deployment-preflight/SKILL.md)<br />`gh skills install github/awesome-copilot azure-deployment-preflight` | Performs comprehensive preflight validation of Bicep deployments to Azure, including template syntax validation, what-if analysis, and permission checks. Use this skill before any deployment to Azure to preview changes, identify potential issues, and ensure the deployment will succeed. Activate when users mention deploying to Azure, validating Bicep files, checking deployment permissions, previewing infrastructure changes, running what-if, or preparing for azd provision. | `references/ERROR-HANDLING.md`<br />`references/REPORT-TEMPLATE.md`<br />`references/VALIDATION-COMMANDS.md` |
-| [azure-devops-cli](../skills/azure-devops-cli/SKILL.md)<br />`gh skills install github/awesome-copilot azure-devops-cli` | Manage Azure DevOps resources via CLI including projects, repos, pipelines, builds, pull requests, work items, artifacts, and service endpoints. Use when working with Azure DevOps, az commands, devops automation, CI/CD, or when user mentions Azure DevOps CLI. | `references/advanced-usage.md`<br />`references/boards-and-iterations.md`<br />`references/org-and-security.md`<br />`references/pipelines-and-builds.md`<br />`references/repos-and-prs.md`<br />`references/variables-and-agents.md`<br />`references/workflows-and-patterns.md` |
+| [azure-devops-cli](../skills/azure-devops-cli/SKILL.md)<br />`gh skills install github/awesome-copilot azure-devops-cli` | Manage Azure DevOps resources via CLI including projects, repos, pipelines, builds, pull requests, work items, artifacts, and service endpoints. Use when working with Azure DevOps, az commands, devops automation, CI/CD, or when user mentions Azure DevOps CLI. | `references/advanced-usage.md`<br />`references/boards-and-iterations.md`<br />`references/long-comments-on-windows.md`<br />`references/org-and-security.md`<br />`references/pipelines-and-builds.md`<br />`references/repos-and-prs.md`<br />`references/variables-and-agents.md`<br />`references/workflows-and-patterns.md` |
 | [azure-pricing](../skills/azure-pricing/SKILL.md)<br />`gh skills install github/awesome-copilot azure-pricing` | Fetches real-time Azure retail pricing using the Azure Retail Prices API (prices.azure.com) and estimates Copilot Studio agent credit consumption. Use when the user asks about the cost of any Azure service, wants to compare SKU prices, needs pricing data for a cost estimate, mentions Azure pricing, Azure costs, Azure billing, or asks about Copilot Studio pricing, Copilot Credits, or agent usage estimation. Covers compute, storage, networking, databases, AI, Copilot Studio, and all other Azure service families. | `references/COPILOT-STUDIO-RATES.md`<br />`references/COST-ESTIMATOR.md`<br />`references/REGIONS.md`<br />`references/SERVICE-NAMES.md` |
 | [azure-resource-health-diagnose](../skills/azure-resource-health-diagnose/SKILL.md)<br />`gh skills install github/awesome-copilot azure-resource-health-diagnose` | Analyze Azure resource health, diagnose issues from logs and telemetry, and create a remediation plan for identified problems. | None |
 | [azure-resource-visualizer](../skills/azure-resource-visualizer/SKILL.md)<br />`gh skills install github/awesome-copilot azure-resource-visualizer` | Analyze Azure resource groups and generate detailed Mermaid architecture diagrams showing the relationships between individual resources. Use this skill when the user asks for a diagram of their Azure resources or help in understanding how the resources relate to each other. | `LICENSE.txt`<br />`assets/template-architecture.md` |
diff --git a/skills/azure-devops-cli/SKILL.md b/skills/azure-devops-cli/SKILL.md
index c8e420fb5..c34f2c40f 100644
--- a/skills/azure-devops-cli/SKILL.md
+++ b/skills/azure-devops-cli/SKILL.md
@@ -92,3 +92,4 @@ Read the relevant reference file based on the user's task. Each file contains co
 | `references/org-and-security.md` | Projects, teams, users, permissions, wikis | Projects, Extensions, Teams, Users, Security groups/permissions, Service endpoints, Wikis, Admin |
 | `references/advanced-usage.md` | Output formatting, JMESPath queries | Output formats, JMESPath queries (basic + advanced), Global args, Common params, Git aliases |
 | `references/workflows-and-patterns.md` | Automation scripts, best practices, error handling | Common workflows, Best practices, Error handling, Scripting patterns, Real-world examples |
+| `references/long-comments-on-windows.md` | Long `--discussion`, `--description`, or `--content` values failing on Windows | The `cmd.exe` 8191 char cap on `az.cmd`, shell detection, and three verified workarounds (`azps.ps1`, native `--file-path`, `az devops invoke --in-file`) |
diff --git a/skills/azure-devops-cli/references/boards-and-iterations.md b/skills/azure-devops-cli/references/boards-and-iterations.md
index b1c99a71a..dc884ba49 100644
--- a/skills/azure-devops-cli/references/boards-and-iterations.md
+++ b/skills/azure-devops-cli/references/boards-and-iterations.md
@@ -56,6 +56,10 @@ az boards work-item create \
   --type Bug \
   --discussion "Initial investigation completed"
 
+# For a long --discussion body on Windows, see references/long-comments-on-windows.md.
+# Short version: use azps.ps1 in PowerShell, or fall back to 'az devops invoke'
+# with --in-file when no native --file-path flag is available.
+
 # Open in browser after creation
 az boards work-item create --title "Bug" --type Bug --open
 ```
@@ -85,6 +89,14 @@ az boards work-item update \
   --id {work-item-id} \
   --discussion "Work in progress"
 
+# Long comment on Windows: read the body into a PowerShell variable and call
+# azps.ps1 instead of az.cmd, or fall back to 'az devops invoke' with --in-file.
+# Full guidance in references/long-comments-on-windows.md.
+#
+# PowerShell example:
+#   $body = Get-Content -Raw .\comment.md
+#   azps.ps1 boards work-item update --id 1234 --discussion $body
+
 # Update with custom fields
 az boards work-item update \
   --id {work-item-id} \
diff --git a/skills/azure-devops-cli/references/long-comments-on-windows.md b/skills/azure-devops-cli/references/long-comments-on-windows.md
new file mode 100644
index 000000000..5fdcd6a8f
--- /dev/null
+++ b/skills/azure-devops-cli/references/long-comments-on-windows.md
@@ -0,0 +1,54 @@
+# Posting Long Comments and Bodies on Windows
+
+On Windows the `az` command resolves to `az.cmd`, a batch wrapper invoked by `cmd.exe`. The whole command line is capped at ~8191 characters, so a long `--discussion`, `--description`, or `--content` value can be silently truncated or fail. Detect the shell before composing a long argument and route accordingly. Skipping this is the most common reason the agent burns 3-5 turns falling back to raw token retrieval and REST calls.
+
+## Detect the shell first
+
+| Environment | Signal | Action |
+|---|---|---|
+| PowerShell on Windows | `$IsWindows -eq $true` and `$PSVersionTable.PSVersion` is set | Use `azps.ps1` (see below) |
+| PowerShell on macOS / Linux | `$IsWindows -eq $false` | Plain `az` is fine, no cmd.exe wrapper |
+| bash / zsh / sh | `$BASH_VERSION` or `$ZSH_VERSION` set, or `uname` works | Plain `az` is fine, no cmd.exe wrapper |
+| Windows `cmd.exe` | `%ComSpec%` ends in `cmd.exe`, no `$PSVersionTable` | Use `azps.ps1` if PowerShell is installed, otherwise see `az devops invoke` fallback below |
+
+## Option 1: `azps.ps1` (PowerShell on Windows)
+
+`azps.ps1` ships with the Azure CLI installer and invokes the Python entry point directly. No `cmd.exe` length cap.
+
+```powershell
+# Read the long body into a variable and pass it through. No quoting headaches.
+$body = Get-Content -Raw .\comment.md
+azps.ps1 boards work-item update --id 1234 --discussion $body
+```
+
+## Option 2: dedicated `--file-path` flag where Azure CLI offers one
+
+Some commands have a native file flag and you should prefer it over any inline body:
+
+- `az devops wiki page create` and `az devops wiki page update` take `--file-path` (with optional `--encoding`).
+- Use it on any shell, including Windows.
+
+```bash
+az devops wiki page create --path 'My page' --wiki myproject --file-path ./page.md --encoding utf-8
+```
+
+## Option 3: `az devops invoke` fallback
+
+When no `--file-path` exists (work-item `--discussion`, PR `--description`) and you're not in PowerShell, post the body via the underlying REST API. `az devops invoke` runs inside the Python entry point, so it isn't subject to the `cmd.exe` cap either, and it takes the request body from a file with `--in-file`:
+
+```bash
+# Post a long discussion comment to work item 1234.
+# REST: POST /{project}/_apis/wit/workItems/{id}/comments?api-version=7.0-preview.3
+az devops invoke \
+  --area wit --resource comments \
+  --route-parameters project={project} workItemId=1234 \
+  --api-version 7.0-preview.3 \
+  --http-method POST \
+  --in-file ./comment.json
+```
+
+Where `comment.json` is `{ "text": "<long markdown body>" }`. This is the universal escape hatch when neither `azps.ps1` nor `--file-path` is available. `az devops invoke` itself accepts `--in-file` natively.
+
+## Don't rely on `@<file>` for plain string args
+
+The Azure CLI `@<file>` convention is documented for JSON parameters (see [the official quoting guide](https://learn.microsoft.com/en-us/cli/azure/use-azure-cli-successfully-quoting)). It is not guaranteed to expand plain string args like `--discussion` or `--description`, so don't reach for it as a substitute for the three options above.