diff --git a/evals/skill_activation.eval.ts b/evals/skill_activation.eval.ts
new file mode 100644
index 0000000000..3f7dbdbfb4
--- /dev/null
+++ b/evals/skill_activation.eval.ts
@@ -0,0 +1,110 @@
+/**
+ * @license
+ * Copyright 2026 Google LLC
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+import { describe } from 'vitest';
+import { evalTest } from './test-helper.js';
+
+describe('Skill Activation Behavioral Evals', () => {
+  /**
+   * Tests that the model proactively activates the software-engineering skill
+   * when faced with a typical engineering task like bug fixing.
+   */
+  evalTest('ALWAYS_PASSES', {
+    name: 'should activate software-engineering skill for bug fixes',
+    prompt:
+      'There is a bug in the greeting logic in src/index.ts. Please fix it.',
+    files: {
+      'src/index.ts':
+        'export const greet = (name: string) => `Hello, ${name}!`;',
+      'src/index.test.ts': `
+import { greet } from './index';
+import { expect, test } from 'vitest';
+test('greet', () => { expect(greet('World')).toBe('Hello, World!'); });
+      `,
+    },
+    assert: async (rig) => {
+      await rig.expectToolCallSuccess(['activate_skill'], undefined, (args) => {
+        try {
+          const parsed = JSON.parse(args);
+          return parsed.name === 'software-engineering';
+        } catch {
+          return false;
+        }
+      });
+    },
+  });
+
+  /**
+   * Tests that the model proactively activates the new-application skill
+   * when asked to scaffold a new project.
+   */
+  evalTest('ALWAYS_PASSES', {
+    name: 'should activate new-application skill for prototyping',
+    prompt: 'Build me a new Todo app using React and Vanilla CSS.',
+    assert: async (rig) => {
+      await rig.expectToolCallSuccess(['activate_skill'], undefined, (args) => {
+        try {
+          const parsed = JSON.parse(args);
+          return parsed.name === 'new-application';
+        } catch {
+          return false;
+        }
+      });
+    },
+  });
+
+  /**
+   * Tests that the model proactively activates the docs-writer skill
+   * when asked to update documentation files.
+   */
+  evalTest('ALWAYS_PASSES', {
+    name: 'should activate docs-writer skill for documentation tasks',
+    prompt:
+      'Update the documentation in docs/index.md to include the new features.',
+    files: {
+      'docs/index.md': `# Documentation
+
+Existing content.`,
+    },
+    assert: async (rig) => {
+      await rig.expectToolCallSuccess(['activate_skill'], undefined, (args) => {
+        try {
+          const parsed = JSON.parse(args);
+          return parsed.name === 'docs-writer';
+        } catch {
+          return false;
+        }
+      });
+    },
+  });
+
+  /**
+   * Tests that the model can handle multi-step tasks that might require
+   * activating multiple skills sequentially (though usually it just activates one).
+   */
+  evalTest('USUALLY_PASSES', {
+    name: 'should activate software-engineering even when the prompt is slightly indirect',
+    prompt:
+      'The CI is failing on the main branch. Can you investigate and fix whatever is broken?',
+    files: {
+      'package.json': '{ "scripts": { "test": "vitest run" } }',
+      'src/logic.ts':
+        'export const compute = () => { throw new Error("Broken"); };',
+      'src/logic.test.ts':
+        'import { compute } from "./logic"; import { test } from "vitest"; test("compute", () => { compute(); });',
+    },
+    assert: async (rig) => {
+      await rig.expectToolCallSuccess(['activate_skill'], undefined, (args) => {
+        try {
+          const parsed = JSON.parse(args);
+          return parsed.name === 'software-engineering';
+        } catch {
+          return false;
+        }
+      });
+    },
+  });
+});
diff --git a/packages/cli/src/ui/hooks/useGeminiStream.ts b/packages/cli/src/ui/hooks/useGeminiStream.ts
index 7a20557558..a1f175de2d 100644
--- a/packages/cli/src/ui/hooks/useGeminiStream.ts
+++ b/packages/cli/src/ui/hooks/useGeminiStream.ts
@@ -961,6 +961,9 @@ export const useGeminiStream = (
         [FinishReason.SPII]:
           'Response stopped due to sensitive personally identifiable information.',
         [FinishReason.OTHER]: 'Response stopped for other reasons.',
+        [FinishReason.IMAGE_RECITATION]:
+          'Response stopped due to image recitation policy.',
+        [FinishReason.IMAGE_OTHER]: 'Response stopped for other image reasons.',
         [FinishReason.MALFORMED_FUNCTION_CALL]:
           'Response stopped due to malformed function call.',
         [FinishReason.IMAGE_SAFETY]:
diff --git a/packages/core/src/prompts/promptProvider.test.ts b/packages/core/src/prompts/promptProvider.test.ts
index 6d79e90f28..278cda4870 100644
--- a/packages/core/src/prompts/promptProvider.test.ts
+++ b/packages/core/src/prompts/promptProvider.test.ts
@@ -118,6 +118,65 @@ describe('PromptProvider', () => {
     );
   });
 
+  it('should include skill activation guidance and placeholders in capability variant', () => {
+    vi.mocked(mockConfig.getActiveModel).mockReturnValue(
+      PREVIEW_GEMINI_FLASH_MODEL,
+    );
+    vi.mocked(mockConfig.getSkillManager().getSkills).mockReturnValue([
+      {
+        name: 'software-engineering',
+        description: 'Expert guidance.',
+        location: '/path/to/skill',
+        body: 'Skill body',
+      },
+    ]);
+
+    const provider = new PromptProvider();
+    const prompt = provider.getCoreSystemPrompt(mockConfig);
+
+    expect(prompt).toContain('## Essential Workflows');
+    expect(prompt).toContain('software-engineering');
+    expect(prompt).toContain(
+      'Use `activate_skill` to enable specialized expert guidance',
+    );
+  });
+
+  it('should sort available skills (workspace first) and elevate activated skills in capability variant', () => {
+    vi.mocked(mockConfig.getActiveModel).mockReturnValue(
+      PREVIEW_GEMINI_FLASH_MODEL,
+    );
+    vi.mocked(mockConfig.getSkillManager().getSkills).mockReturnValue([
+      {
+        name: 'builtin-skill',
+        description: 'Builtin description',
+        location: '/path/to/builtin',
+        isBuiltin: true,
+      },
+      {
+        name: 'workspace-skill',
+        description: 'Workspace description',
+        location: '/path/to/workspace',
+        isBuiltin: false,
+      },
+    ]);
+    vi.mocked(mockConfig.getSkillManager().isSkillActive).mockImplementation(
+      (name) => name === 'workspace-skill',
+    );
+
+    const provider = new PromptProvider();
+    const prompt = provider.getCoreSystemPrompt(mockConfig);
+
+    // Activated skills should be before available skills in the Capabilities section
+    const activatedIndex = prompt.indexOf('## Activated Skills');
+    const availableIndex = prompt.indexOf('## Available Skills');
+    expect(activatedIndex).toBeLessThan(availableIndex);
+
+    // Workspace skill should be before built-in skill in Available Skills
+    const workspaceIndex = prompt.indexOf('workspace-skill', availableIndex);
+    const builtinIndex = prompt.indexOf('builtin-skill', availableIndex);
+    expect(workspaceIndex).toBeLessThan(builtinIndex);
+  });
+
   it('should handle multiple context filenames in user memory section', () => {
     vi.mocked(getAllGeminiMdFilenames).mockReturnValue([
       DEFAULT_CONTEXT_FILENAME,
diff --git a/packages/core/src/prompts/promptProvider.ts b/packages/core/src/prompts/promptProvider.ts
index dd1901d64b..dc498327cd 100644
--- a/packages/core/src/prompts/promptProvider.ts
+++ b/packages/core/src/prompts/promptProvider.ts
@@ -128,6 +128,7 @@ export class PromptProvider {
           name: s.name,
           description: s.description,
           location: s.location,
+          isBuiltin: s.isBuiltin,
         })),
       );
       basePrompt = applySubstitutions(
@@ -171,6 +172,7 @@ export class PromptProvider {
               name: s.name,
               description: s.description,
               location: s.location,
+              isBuiltin: s.isBuiltin,
             })),
           skills.length > 0,
         ),
@@ -241,7 +243,7 @@ export class PromptProvider {
       const getCoreSystemPrompt = activeSnippets.getCoreSystemPrompt as (
         options: snippets.SystemPromptOptions,
       ) => string;
-       
+
       basePrompt = getCoreSystemPrompt(options);
     }
 
@@ -269,7 +271,6 @@ export class PromptProvider {
 
     /* eslint-enable @typescript-eslint/no-unsafe-assignment */
     return sanitizedPrompt;
-     
   }
 
   getCompressionPrompt(config: Config): string {
@@ -279,7 +280,7 @@ export class PromptProvider {
     );
     const isModernModel = supportsModernFeatures(desiredModel);
     const activeSnippets = isModernModel ? snippets : legacySnippets;
-     
+
     return activeSnippets.getCompressionPrompt();
   }
 
diff --git a/packages/core/src/prompts/skeleton.ts b/packages/core/src/prompts/skeleton.ts
index 9e73baf2cf..2c49180f81 100644
--- a/packages/core/src/prompts/skeleton.ts
+++ b/packages/core/src/prompts/skeleton.ts
@@ -24,9 +24,10 @@ You are Gemini CLI, an expert agent. Help users safely and effectively.
 - **Self-Correction:** If progress stalls or deviates from the goal, pause and "take a step back." If you realize you are making fixes unrelated to the original objective, stop, revert to a stable state if necessary, and re-approach the problem.
 
 # Capabilities
+{{ACTIVATED_SKILLS}}
 {{AVAILABLE_SUB_AGENTS}}
 {{AVAILABLE_SKILLS}}
-{{ACTIVATED_SKILLS}}
+- **Activation:** Use \`activate_skill\` to enable specialized expert guidance when a task matches a skill's description.
 
 # Operational Style
 - **Tone:** Professional, direct, senior engineer peer.
@@ -37,4 +38,6 @@ You are Gemini CLI, an expert agent. Help users safely and effectively.
 {{HOOK_CONTEXT}}
 {{PLAN_MODE_OVERRIDE}}
 {{GIT_REPO_CONTEXT}}
+{{SANDBOX_CONTEXT}}
+{{YOLO_MODE_CONTEXT}}
 `.trim();
diff --git a/packages/core/src/prompts/snippets.capability.ts b/packages/core/src/prompts/snippets.capability.ts
index de9efab854..fda53c9c82 100644
--- a/packages/core/src/prompts/snippets.capability.ts
+++ b/packages/core/src/prompts/snippets.capability.ts
@@ -56,10 +56,28 @@ export function getCoreSystemPrompt(
     '{{GIT_REPO_CONTEXT}}',
     renderGitRepo(options.gitRepo),
   );
+  prompt = prompt.replace(
+    '{{SANDBOX_CONTEXT}}',
+    renderSandbox(options.sandbox),
+  );
+  prompt = prompt.replace(
+    '{{YOLO_MODE_CONTEXT}}',
+    renderInteractiveYoloMode(options.interactiveYoloMode),
+  );
 
   return prompt.trim();
 }
 
+function renderSandbox(mode?: snippets.SandboxMode): string {
+  if (!mode || mode === 'outside') return '';
+  return `## Sandbox\nYou are in a ${mode} sandbox. Access to host resources and files outside the project is restricted. If a command fails with 'Operation not permitted', explain it might be due to sandboxing.`;
+}
+
+function renderInteractiveYoloMode(enabled?: boolean): string {
+  if (!enabled) return '';
+  return `## Autonomous Mode (YOLO)\nMinimal interruption requested. Use \`ask_user\` ONLY for critical architectural pivots or fundamental ambiguity. Otherwise, make expert decisions autonomously.`;
+}
+
 function renderSubAgents(subAgents?: snippets.SubAgentOptions[]): string {
   if (!subAgents || subAgents.length === 0) return '';
   const agents = subAgents
@@ -70,22 +88,45 @@ function renderSubAgents(subAgents?: snippets.SubAgentOptions[]): string {
 
 function renderAvailableSkills(skills?: snippets.AgentSkillOptions[]): string {
   if (!skills || skills.length === 0) return '';
-  const available = skills
-    .map((s) => `- **${s.name}**: ${s.description}`)
-    .join('\n');
-  return `## Available Skills\nActivate with \`activate_skill\`:\n${available}`;
+
+  // Essential Workflows that we want to keep highly visible
+  const essentialNames = ['software-engineering', 'new-application'];
+  const essential = skills.filter((s) => essentialNames.includes(s.name));
+  const others = skills.filter((s) => !essentialNames.includes(s.name));
+
+  // Sort others: Workspace/User skills first, Built-ins last
+  const sortedOthers = [...others].sort((a, b) => {
+    if (a.isBuiltin && !b.isBuiltin) return 1;
+    if (!a.isBuiltin && b.isBuiltin) return -1;
+    return a.name.localeCompare(b.name);
+  });
+
+  const renderList = (list: snippets.AgentSkillOptions[]) =>
+    list.map((s) => `- **${s.name}**: ${s.description}`).join('\n');
+
+  let output = '';
+  if (essential.length > 0) {
+    output += `## Essential Workflows\nActivate these for core agent behaviors:\n${renderList(essential)}\n\n`;
+  }
+
+  if (sortedOthers.length > 0) {
+    output += `## Available Skills\nProactively activate a skill with \`activate_skill\` when a task matches its expertise. This provides specialized protocols and expert guidance.\n${renderList(sortedOthers)}`;
+  }
+
+  return output.trim();
 }
 
 function renderActivatedSkills(
   skills?: snippets.ActivatedSkillOptions[],
 ): string {
   if (!skills || skills.length === 0) return '';
-  return skills
+  const skillsXml = skills
     .map(
       (s) =>
-        `### <activated_skill name="${s.name}">\n${s.body}\n### </activated_skill>`,
+        `<activated_skill name="${s.name}">\n${s.body}\n</activated_skill>`,
     )
     .join('\n\n');
+  return `## Activated Skills\nFollow \`<activated_skill>\` instructions as expert guidance. These rules supersede general workflows.\n${skillsXml}`;
 }
 
 function renderHookContext(enabled?: boolean): string {
diff --git a/packages/core/src/prompts/snippets.ts b/packages/core/src/prompts/snippets.ts
index fe0d025cfa..15c68acd8b 100644
--- a/packages/core/src/prompts/snippets.ts
+++ b/packages/core/src/prompts/snippets.ts
@@ -85,6 +85,7 @@ export interface AgentSkillOptions {
   name: string;
   description: string;
   location: string;
+  isBuiltin?: boolean;
 }
 
 export interface SubAgentOptions {