diff --git a/webui/src/web-components/demo/sketch-timeline.demo.html b/webui/src/web-components/demo/sketch-timeline.demo.html
index 58ff5d9..9c817d8 100644
--- a/webui/src/web-components/demo/sketch-timeline.demo.html
+++ b/webui/src/web-components/demo/sketch-timeline.demo.html
@@ -8,38 +8,129 @@
         {
           type: "user",
           content: "a user message",
+          timestamp: "2025-04-14T16:39:30.639533919Z",
+          conversation_id: "conv-123456",
+          idx: 0,
         },
         {
           type: "agent",
-          content: "an agent message",
+          content: "an agent message with usage information",
+          timestamp: "2025-04-14T16:39:31.639533919Z",
+          conversation_id: "conv-123456",
+          idx: 1,
+          usage: {
+            input_tokens: 4,
+            cache_creation_input_tokens: 2620,
+            cache_read_input_tokens: 0,
+            output_tokens: 106,
+            cost_usd: 0.011427,
+          },
         },
         {
           type: "agent",
-          content: "an agent message",
+          content: "an agent message with a single tool call",
+          timestamp: "2025-04-14T16:39:32.639533919Z",
+          conversation_id: "conv-123456",
+          idx: 2,
+          tool_calls: [
+            {
+              name: "bash",
+              input: 'find . -type f -name "*.go" | wc -l',
+              tool_call_id: "call_12345",
+              args: '{"command": "find . -type f -name \\"*.go\\" | wc -l"}',
+              result: "486",
+            },
+          ],
         },
         {
           type: "agent",
-          content: "an agent message",
+          content:
+            "an agent message with a bash command that is extremely long and would create a horizontal scrollbar",
+          timestamp: "2025-04-14T16:39:32.739533919Z",
+          conversation_id: "conv-123456",
+          idx: 2.5,
+          tool_calls: [
+            {
+              name: "bash",
+              input:
+                'find /app -type f -name "*.ts" -o -name "*.js" -o -name "*.tsx" -o -name "*.jsx" | xargs grep -l "useState" | while read file; do echo "File: $file"; grep -n "useState" $file | head -5; echo; done | head -50',
+              tool_call_id: "call_verylongbash",
+              args: '{"command": "find /app -type f -name \\"*.ts\\" -o -name \\"*.js\\" -o -name \\"*.tsx\\" -o -name \\"*.jsx\\" | xargs grep -l \\"useState\\" | while read file; do echo \\"File: $file\\"; grep -n \\"useState\\" $file | head -5; echo; done | head -50"}',
+              result:
+                'File: /app/webui/src/web-components/sketch-chat-input.ts\n97:  useState,\n\nFile: /app/webui/src/web-components/sketch-diff-view.ts\n47:import { createRef, ref, useState } from "lit/directives/ref.js";\n110:  const [selectedFiles, setSelectedFiles] = useState([]);\n',
+            },
+          ],
+        },
+        {
+          type: "agent",
+          content:
+            "an agent message with a bash command that has a very long output that would create a horizontal scrollbar",
+          timestamp: "2025-04-14T16:39:32.839533919Z",
+          conversation_id: "conv-123456",
+          idx: 2.7,
+          tool_calls: [
+            {
+              name: "bash",
+              input: "cat /app/webui/package.json | grep -A 5 dependencies",
+              tool_call_id: "call_longoutput",
+              args: '{"command": "cat /app/webui/package.json | grep -A 5 dependencies"}',
+              result:
+                '  "dependencies": {\n    "@xterm/addon-fit": "^0.10.0",\n    "@xterm/xterm": "^5.5.0",\n    "diff2html": "3.4.51",\n    "lit": "^3.2.1",\n    "marked": "^15.0.7",\n    "mermaid": "^11.6.0",\n    "sanitize-html": "^2.15.0",\n    "vega": "^5.33.0",\n    "vega-embed": "^6.29.0",\n    "vega-lite": "^5.23.0",\n    "react": "^18.2.0",\n    "react-dom": "^18.2.0",\n    "styled-components": "^6.1.8",\n    "tailwindcss": "^3.4.1",\n    "typescript": "^5.3.3",\n    "zod": "^3.22.4",\n    "@types/react": "^18.2.55",\n    "@types/react-dom": "^18.2.19",\n    "eslint": "^8.56.0",\n    "prettier": "^3.2.5"\n  },',
+            },
+          ],
+        },
+        {
+          type: "agent",
+          content:
+            "an agent message with two tool calls that will show how the width behaves with very long content that should push the boundaries of the UI layout with really wide tool calls that might stretch beyond the regular message content width",
+          timestamp: "2025-04-14T16:39:33.639533919Z",
+          conversation_id: "conv-123456",
+          idx: 3,
+          tool_calls: [
+            {
+              name: "keyword_search",
+              input: "Search for files related to the timeline component",
+              tool_call_id: "call_67890",
+              args: '{"query": "Find all files related to the timeline component in the project", "search_terms": ["timeline", "message", "component", "web-components"]}',
+              result:
+                "Found 3 files: sketch-timeline.ts, sketch-timeline-message.ts, sketch-timeline.demo.html",
+            },
+            {
+              name: "patch",
+              input: "Update the timeline component CSS",
+              tool_call_id: "call_abcdef",
+              args: '{"path": "/app/webui/src/web-components/sketch-timeline.ts", "patches": [{"operation": "replace", "oldText": "width: 100%;", "newText": "width: auto; max-width: 100%;"}, {"operation": "replace", "oldText": "margin-bottom: 20px;", "newText": "margin-bottom: 24px;"}]}',
+              result: "Applied all patches successfully",
+            },
+          ],
         },
         {
           type: "user",
-          content: "a user message",
-        },
-        {
-          type: "user",
-          content: "a user message",
+          content: "another user message",
+          timestamp: "2025-04-14T16:39:34.639533919Z",
+          conversation_id: "conv-123456",
+          idx: 4,
         },
         {
           type: "agent",
-          content: "an agent message",
-        },
-        {
-          type: "user",
-          content: "a user message",
+          content: "an agent message with detailed information and usage data",
+          timestamp: "2025-04-14T16:39:35.639533919Z",
+          conversation_id: "conv-123456",
+          idx: 5,
+          usage: {
+            input_tokens: 125,
+            cache_creation_input_tokens: 0,
+            cache_read_input_tokens: 3050,
+            output_tokens: 245,
+            cost_usd: 0.023456,
+          },
         },
         {
           type: "tool",
           content: "a tool use message",
+          timestamp: "2025-04-14T16:39:36.639533919Z",
+          conversation_id: "conv-123456",
+          idx: 6,
         },
         {
           type: "commit",
@@ -54,14 +145,24 @@
                 "sketch/create-readmemd-for-web-components-directory",
             },
           ],
-          timestamp: "2025-04-14T16:39:33.639533919Z",
-          conversation_id: "",
-          idx: 17,
+          timestamp: "2025-04-14T16:39:37.639533919Z",
+          conversation_id: "conv-123456",
+          idx: 7,
         },
         {
           type: "agent",
           content: "an end-of-turn agent message",
           end_of_turn: true,
+          timestamp: "2025-04-14T16:39:38.639533919Z",
+          conversation_id: "conv-123456",
+          idx: 8,
+          usage: {
+            input_tokens: 85,
+            cache_creation_input_tokens: 1240,
+            cache_read_input_tokens: 750,
+            output_tokens: 178,
+            cost_usd: 0.018976,
+          },
         },
       ];