diff --git a/loop/agent.go b/loop/agent.go
index 7270bfd..4ad1341 100644
--- a/loop/agent.go
+++ b/loop/agent.go
@@ -2401,6 +2401,7 @@
 	InitialCommit      string
 	Codebase           *onstart.Codebase
 	UseSketchWIP       bool
+	InstallationNudge  bool
 	Branch             string
 	SpecialInstruction string
 }
@@ -2408,13 +2409,14 @@
 // renderSystemPrompt renders the system prompt template.
 func (a *Agent) renderSystemPrompt() string {
 	data := systemPromptData{
-		ClientGOOS:    a.config.ClientGOOS,
-		ClientGOARCH:  a.config.ClientGOARCH,
-		WorkingDir:    a.workingDir,
-		RepoRoot:      a.repoRoot,
-		InitialCommit: a.SketchGitBase(),
-		Codebase:      a.codebase,
-		UseSketchWIP:  a.config.InDocker,
+		ClientGOOS:        a.config.ClientGOOS,
+		ClientGOARCH:      a.config.ClientGOARCH,
+		WorkingDir:        a.workingDir,
+		RepoRoot:          a.repoRoot,
+		InitialCommit:     a.SketchGitBase(),
+		Codebase:          a.codebase,
+		UseSketchWIP:      a.config.InDocker,
+		InstallationNudge: a.config.InDocker,
 	}
 	now := time.Now()
 	if now.Month() == time.September && now.Day() == 19 {
diff --git a/loop/agent_system_prompt.txt b/loop/agent_system_prompt.txt
index f2bd7ed..8a39879 100644
--- a/loop/agent_system_prompt.txt
+++ b/loop/agent_system_prompt.txt
@@ -43,6 +43,12 @@
 Commit work to the 'sketch-wip' branch. Changes on other branches will not be pushed to the user.
 {{ end }}
 
+{{ if .InstallationNudge }}
+For programming platform versions, install the required versions rather than giving up. 
+Suggest to the user that they update dear_llm.md or set up a custom container image
+with the platform versions they require.
+{{ end }}
+
 When communicating with the user, take it easy on the emoji, don't be over-enthusiastic, and be concise.
 
 Docker is available. Before running the docker command, start dockerd as a background process.
diff --git a/loop/testdata/agent_loop.httprr b/loop/testdata/agent_loop.httprr
index b523252..8382fa8 100644
--- a/loop/testdata/agent_loop.httprr
+++ b/loop/testdata/agent_loop.httprr
@@ -1,9 +1,9 @@
 httprr trace v1
-18101 2303
+18105 2423
 POST https://api.anthropic.com/v1/messages HTTP/1.1
 Host: api.anthropic.com
 User-Agent: Go-http-client/1.1
-Content-Length: 17903
+Content-Length: 17907
 Anthropic-Version: 2023-06-01
 Content-Type: application/json
 
@@ -546,7 +546,7 @@
  ],
  "system": [
   {
-   "text": "You are the expert software engineer and architect powering Sketch,\nan agentic coding environment that helps users accomplish coding tasks through autonomous analysis and implementation.\n\n\u003cworkflow\u003e\nStart by asking concise clarifying questions as needed.\nOnce the intent is clear, work autonomously.\nWhenever possible, do end-to-end testing, to ensure fully working functionality.\nAim for a small diff size while thoroughly completing the requested task.\nPrioritize thoughtful analysis and critical engagement over agreeability.\n\nBreak down the overall goal into a series of smaller steps.\nUse the todo_read and todo_write tools to organize and track your work systematically.\n\nFollow this broad workflow:\n\n- Think about how the current step fits into the overall plan.\n- Do research. Good tool choices: bash, think, keyword_search\n- Make edits.\n- If you have completed a standalone chunk of work, make a git commit.\n- Update your todo task list.\n- Repeat.\n\nTo make edits reliably and efficiently, first think about the intent of the edit,\nand what set of patches will achieve that intent.\nThen use the patch tool to make those edits. Combine all edits to any given file into a single patch tool call.\n\nYou may run tool calls in parallel.\n\nComplete every task exhaustively - no matter how repetitive or tedious.\nPartial work, pattern demonstrations, or stubs with TODOs are not acceptable, unless explicitly permitted by the user.\n\nThe done tool provides a checklist of items you MUST verify and\nreview before declaring that you are done. Before executing\nthe done tool, run all the tools the done tool checklist asks\nfor, including creating a git commit. Do not forget to run tests.\n\n\n\nWhen communicating with the user, take it easy on the emoji, don't be over-enthusiastic, and be concise.\n\nDocker is available. Before running the docker command, start dockerd as a background process.\nAlways use --network=host when running docker containers.\n\u003c/workflow\u003e\n\n\u003cstyle\u003e\nDefault coding guidelines:\n- Clear is better than clever.\n- Minimal inline comments: non-obvious logic and key decisions only.\n- When no commit message style guidance is provided: write a single lowercase line starting with an imperative verb, ≤50 chars, no period\n\u003c/style\u003e\n\n\u003csystem_info\u003e\n\u003cplatform\u003e\nlinux/amd64\n\u003c/platform\u003e\n\u003cpwd\u003e\n/\n\u003c/pwd\u003e\n\u003c/system_info\u003e\n\n\u003cgit_info\u003e\n\u003cgit_root\u003e\n\n\u003c/git_root\u003e\n\u003cHEAD\u003e\nHEAD\n\u003c/HEAD\u003e\n\n\u003c/git_info\u003e\n\n",
+   "text": "You are the expert software engineer and architect powering Sketch,\nan agentic coding environment that helps users accomplish coding tasks through autonomous analysis and implementation.\n\n\u003cworkflow\u003e\nStart by asking concise clarifying questions as needed.\nOnce the intent is clear, work autonomously.\nWhenever possible, do end-to-end testing, to ensure fully working functionality.\nAim for a small diff size while thoroughly completing the requested task.\nPrioritize thoughtful analysis and critical engagement over agreeability.\n\nBreak down the overall goal into a series of smaller steps.\nUse the todo_read and todo_write tools to organize and track your work systematically.\n\nFollow this broad workflow:\n\n- Think about how the current step fits into the overall plan.\n- Do research. Good tool choices: bash, think, keyword_search\n- Make edits.\n- If you have completed a standalone chunk of work, make a git commit.\n- Update your todo task list.\n- Repeat.\n\nTo make edits reliably and efficiently, first think about the intent of the edit,\nand what set of patches will achieve that intent.\nThen use the patch tool to make those edits. Combine all edits to any given file into a single patch tool call.\n\nYou may run tool calls in parallel.\n\nComplete every task exhaustively - no matter how repetitive or tedious.\nPartial work, pattern demonstrations, or stubs with TODOs are not acceptable, unless explicitly permitted by the user.\n\nThe done tool provides a checklist of items you MUST verify and\nreview before declaring that you are done. Before executing\nthe done tool, run all the tools the done tool checklist asks\nfor, including creating a git commit. Do not forget to run tests.\n\n\n\n\n\nWhen communicating with the user, take it easy on the emoji, don't be over-enthusiastic, and be concise.\n\nDocker is available. Before running the docker command, start dockerd as a background process.\nAlways use --network=host when running docker containers.\n\u003c/workflow\u003e\n\n\u003cstyle\u003e\nDefault coding guidelines:\n- Clear is better than clever.\n- Minimal inline comments: non-obvious logic and key decisions only.\n- When no commit message style guidance is provided: write a single lowercase line starting with an imperative verb, ≤50 chars, no period\n\u003c/style\u003e\n\n\u003csystem_info\u003e\n\u003cplatform\u003e\nlinux/amd64\n\u003c/platform\u003e\n\u003cpwd\u003e\n/\n\u003c/pwd\u003e\n\u003c/system_info\u003e\n\n\u003cgit_info\u003e\n\u003cgit_root\u003e\n\n\u003c/git_root\u003e\n\u003cHEAD\u003e\nHEAD\n\u003c/HEAD\u003e\n\n\u003c/git_info\u003e\n\n",
    "type": "text",
    "cache_control": {
     "type": "ephemeral"
@@ -557,24 +557,24 @@
 Anthropic-Organization-Id: 3c473a21-7208-450a-a9f8-80aebda45c1b
 Anthropic-Ratelimit-Input-Tokens-Limit: 2000000
 Anthropic-Ratelimit-Input-Tokens-Remaining: 2000000
-Anthropic-Ratelimit-Input-Tokens-Reset: 2025-07-24T22:15:37Z
+Anthropic-Ratelimit-Input-Tokens-Reset: 2025-07-24T23:55:06Z
 Anthropic-Ratelimit-Output-Tokens-Limit: 400000
 Anthropic-Ratelimit-Output-Tokens-Remaining: 400000
-Anthropic-Ratelimit-Output-Tokens-Reset: 2025-07-24T22:15:42Z
+Anthropic-Ratelimit-Output-Tokens-Reset: 2025-07-24T23:55:10Z
 Anthropic-Ratelimit-Requests-Limit: 4000
 Anthropic-Ratelimit-Requests-Remaining: 3999
-Anthropic-Ratelimit-Requests-Reset: 2025-07-24T22:15:36Z
+Anthropic-Ratelimit-Requests-Reset: 2025-07-24T23:55:05Z
 Anthropic-Ratelimit-Tokens-Limit: 2400000
 Anthropic-Ratelimit-Tokens-Remaining: 2400000
-Anthropic-Ratelimit-Tokens-Reset: 2025-07-24T22:15:37Z
+Anthropic-Ratelimit-Tokens-Reset: 2025-07-24T23:55:06Z
 Cf-Cache-Status: DYNAMIC
-Cf-Ray: 9646c6f5691fce74-SJC
+Cf-Ray: 964758ac38ba7acd-SJC
 Content-Type: application/json
-Date: Thu, 24 Jul 2025 22:15:42 GMT
-Request-Id: req_011CRScfwLXsX2Ug7WSdEZnN
+Date: Thu, 24 Jul 2025 23:55:10 GMT
+Request-Id: req_011CRSkFtyQxXFGwZsBb7RY3
 Server: cloudflare
 Strict-Transport-Security: max-age=31536000; includeSubDomains; preload
 Via: 1.1 google
 X-Robots-Tag: none
 
-{"id":"msg_01So9qajkJgERbHBwNUwEkmF","type":"message","role":"assistant","model":"claude-sonnet-4-20250514","content":[{"type":"text","text":"Here are the tools available to me:\n\n**File & Code Management:**\n- `bash` - Execute shell commands\n- `keyword_search` - Search for files/content in codebases\n- `patch` - Modify files with precise text edits\n\n**Task Management:**\n- `think` - Record thoughts and plans\n- `todo_read` / `todo_write` - Manage task lists\n- `done` - Mark completion with checklist verification\n\n**Development Workflow:**\n- `codereview` - Run automated code review\n- `about_sketch` - Get help with Sketch functionality\n\n**Browser Automation:**\n- `browser_navigate` - Navigate to URLs\n- `browser_click` / `browser_type` - Interact with elements\n- `browser_wait_for` / `browser_get_text` - Wait for and read content\n- `browser_eval` - Execute JavaScript\n- `browser_scroll_into_view` / `browser_resize` - Control viewport\n- `browser_take_screenshot` / `read_image` - Capture and read images\n- `browser_recent_console_logs` / `browser_clear_console_logs` - Access console output"}],"stop_reason":"end_turn","stop_sequence":null,"usage":{"input_tokens":3,"cache_creation_input_tokens":4142,"cache_read_input_tokens":0,"output_tokens":269,"service_tier":"standard"}}
\ No newline at end of file
+{"id":"msg_01KEJ5q4EwEz9kvMsouiGC9P","type":"message","role":"assistant","model":"claude-sonnet-4-20250514","content":[{"type":"text","text":"Here are the tools available to me:\n\n**File & Code Management:**\n- `bash` - Execute shell commands\n- `keyword_search` - Search files by keywords/concepts\n- `patch` - Modify files with precise text edits\n\n**Task Management:**\n- `think` - Internal note-taking and planning\n- `todo_read` / `todo_write` - Track and manage task lists\n- `done` - Mark completion with checklist verification\n- `codereview` - Run automated code review\n\n**Browser Automation:**\n- `browser_navigate` - Navigate to URLs\n- `browser_click` - Click elements\n- `browser_type` - Type into input fields\n- `browser_wait_for` - Wait for elements\n- `browser_get_text` - Read element text\n- `browser_eval` - Execute JavaScript\n- `browser_scroll_into_view` - Scroll to elements\n- `browser_resize` - Resize browser window\n- `browser_recent_console_logs` - Get console logs\n- `browser_clear_console_logs` - Clear console logs\n- `browser_take_screenshot` - Capture screenshots\n\n**Media:**\n- `read_image` - Read and encode image files\n\n**Help:**\n- `about_sketch` - Get information about Sketch environment"}],"stop_reason":"end_turn","stop_sequence":null,"usage":{"input_tokens":3,"cache_creation_input_tokens":4142,"cache_read_input_tokens":0,"output_tokens":296,"service_tier":"standard"}}
\ No newline at end of file