diff --git a/public/index.html b/public/index.html
index 730fb78..cf8663b 100644
--- a/public/index.html
+++ b/public/index.html
@@ -144,7 +144,7 @@
 
     .prompt {
       background: #2a2a2a;
-      border: 1px solid #ff9800;
+      border: 2px solid #ff9800;
       border-radius: 8px;
       padding: 16px;
       margin-bottom: 12px;
@@ -156,6 +156,93 @@
       line-height: 1.5;
     }
 
+    .prompt-header {
+      font-size: 16px;
+      font-weight: 600;
+      margin-bottom: 12px;
+      color: #ff9800;
+    }
+
+    .prompt-tool {
+      font-size: 14px;
+      font-weight: 600;
+      margin-bottom: 8px;
+      color: #888;
+    }
+
+    .prompt-tool-name {
+      color: #e0e0e0;
+    }
+
+    .prompt-tool-input {
+      font-size: 13px;
+      font-family: "SF Mono", Monaco, "Cascadia Code", "Courier New", monospace;
+      color: #888;
+      margin-bottom: 12px;
+      word-break: break-all;
+    }
+
+    .prompt-question {
+      font-size: 14px;
+      margin-bottom: 16px;
+      line-height: 1.5;
+    }
+
+    .prompt-options {
+      margin-bottom: 16px;
+    }
+
+    .prompt-option {
+      display: flex;
+      align-items: center;
+      gap: 12px;
+      padding: 12px;
+      border: 1px solid #3a3a3a;
+      border-radius: 6px;
+      margin-bottom: 8px;
+      min-height: 48px;
+      cursor: pointer;
+      user-select: none;
+      transition: background 0.2s;
+    }
+
+    .prompt-option:hover {
+      background: rgba(255, 255, 255, 0.05);
+    }
+
+    .prompt-option input[type="radio"],
+    .prompt-option input[type="checkbox"] {
+      width: 20px;
+      height: 20px;
+      margin: 0;
+      cursor: pointer;
+      flex-shrink: 0;
+    }
+
+    .prompt-option-label {
+      flex: 1;
+      font-size: 14px;
+      line-height: 1.5;
+      cursor: pointer;
+    }
+
+    .prompt-other-input {
+      width: 100%;
+      padding: 12px;
+      margin-top: 8px;
+      border: 1px solid #3a3a3a;
+      border-radius: 6px;
+      background: #1a1a1a;
+      color: #e0e0e0;
+      font-size: 14px;
+      font-family: inherit;
+    }
+
+    .prompt-other-input:focus {
+      outline: none;
+      border-color: #ff9800;
+    }
+
     .prompt-actions {
       display: flex;
       gap: 8px;
@@ -169,7 +256,7 @@
       font-size: 16px;
       font-weight: 600;
       cursor: pointer;
-      min-height: 44px;
+      min-height: 48px;
       transition: opacity 0.2s;
     }
 
@@ -177,6 +264,11 @@
       opacity: 0.7;
     }
 
+    .btn:disabled {
+      opacity: 0.5;
+      cursor: not-allowed;
+    }
+
     .btn-approve {
       background: #4CAF50;
       color: white;
@@ -187,6 +279,34 @@
       color: white;
     }
 
+    .btn-submit {
+      background: #ff9800;
+      color: white;
+    }
+
+    .btn-secondary {
+      background: #3a3a3a;
+      color: #e0e0e0;
+      position: relative;
+    }
+
+    .btn-secondary[data-tooltip]:hover::after {
+      content: attr(data-tooltip);
+      position: absolute;
+      bottom: 100%;
+      left: 50%;
+      transform: translateX(-50%);
+      margin-bottom: 8px;
+      padding: 8px 12px;
+      background: #1a1a1a;
+      color: #e0e0e0;
+      font-size: 12px;
+      white-space: nowrap;
+      border-radius: 4px;
+      border: 1px solid #3a3a3a;
+      z-index: 1000;
+    }
+
     .empty-state {
       padding: 32px 16px;
       text-align: center;
@@ -208,7 +328,7 @@
       .session,
       .prompt {
         background: white;
-        border-color: #e0e0e0;
+        border-color: #ff9800;
       }
 
       .session-output {
@@ -219,6 +339,24 @@
       .terminal {
         color: #1a1a1a;
       }
+
+      .prompt-option {
+        border-color: #e0e0e0;
+      }
+
+      .prompt-option:hover {
+        background: rgba(0, 0, 0, 0.05);
+      }
+
+      .prompt-other-input {
+        background: white;
+        border-color: #e0e0e0;
+        color: #1a1a1a;
+      }
+
+      .prompt-tool-input {
+        color: #666;
+      }
     }
   </style>
 </head>
@@ -328,6 +466,7 @@
           id: data.prompt_id,
           session_id: data.session_id,
           text: data.prompt_text,
+          json: data.prompt_json ? JSON.parse(data.prompt_json) : null,
         });
         renderPrompts();
       });
@@ -397,17 +536,260 @@
         return;
       }
 
-      $prompts.innerHTML = Array.from(state.prompts.values()).map(p => `
+      $prompts.innerHTML = Array.from(state.prompts.values()).map(p => {
+        if (p.json) {
+          return renderRichPrompt(p);
+        } else {
+          // Fallback for old-style prompts
+          return `
+            <div class="prompt" data-prompt="${p.id}">
+              <div class="prompt-text">${escapeHtml(p.text)}</div>
+              <div class="prompt-actions">
+                <button class="btn btn-approve" onclick="respondToPrompt('${p.id}', 'approve')">Approve</button>
+                <button class="btn btn-reject" onclick="respondToPrompt('${p.id}', 'reject')">Reject</button>
+              </div>
+            </div>
+          `;
+        }
+      }).join('');
+    }
+
+    function renderRichPrompt(p) {
+      const json = p.json;
+      const promptType = json.prompt_type;
+
+      if (promptType === 'permission') {
+        return renderPermissionPrompt(p);
+      } else if (promptType === 'question') {
+        return renderQuestionPrompt(p);
+      } else if (promptType === 'exit_plan') {
+        return renderExitPlanPrompt(p);
+      } else {
+        // Unknown type, fallback
+        return `
+          <div class="prompt" data-prompt="${p.id}">
+            <div class="prompt-text">${escapeHtml(p.text)}</div>
+            <div class="prompt-actions">
+              <button class="btn btn-approve" onclick="respondToPrompt('${p.id}', 'approve')">Approve</button>
+              <button class="btn btn-reject" onclick="respondToPrompt('${p.id}', 'reject')">Reject</button>
+            </div>
+          </div>
+        `;
+      }
+    }
+
+    function renderPermissionPrompt(p) {
+      const json = p.json;
+      const toolName = json.tool_name || 'Unknown';
+      const toolInput = json.tool_input || {};
+      const options = json.options || [];
+      const selectedOption = json.selected_option;
+      const allowsTabInstructions = json.allows_tab_instructions || false;
+
+      // Extract relevant tool input info
+      let toolInputDisplay = '';
+      if (toolName === 'Write' || toolName === 'Edit' || toolName === 'Read') {
+        toolInputDisplay = toolInput.file_path || '';
+      } else if (toolName === 'Bash') {
+        toolInputDisplay = toolInput.command || '';
+      } else if (toolInput.path) {
+        toolInputDisplay = toolInput.path;
+      }
+
+      const optionsHtml = options.map((opt, idx) => `
+        <label class="prompt-option" onclick="selectOption('${p.id}', ${idx})">
+          <input type="radio" name="prompt-${p.id}" value="${escapeHtml(opt.value)}" ${opt.value === selectedOption ? 'checked' : ''}>
+          <span class="prompt-option-label">${escapeHtml(opt.label)}</span>
+        </label>
+      `).join('');
+
+      return `
         <div class="prompt" data-prompt="${p.id}">
-          <div class="prompt-text">${escapeHtml(p.text)}</div>
+          <div class="prompt-tool">Tool: <span class="prompt-tool-name">${escapeHtml(toolName)}</span></div>
+          ${toolInputDisplay ? `<div class="prompt-tool-input">${escapeHtml(toolInputDisplay)}</div>` : ''}
+          <div class="prompt-question">${escapeHtml(p.text)}</div>
+          <div class="prompt-options">
+            ${optionsHtml}
+          </div>
           <div class="prompt-actions">
-            <button class="btn btn-approve" onclick="respondToPrompt('${p.id}', 'approve')">Approve</button>
-            <button class="btn btn-reject" onclick="respondToPrompt('${p.id}', 'reject')">Reject</button>
+            <button class="btn btn-submit" onclick="submitRichPrompt('${p.id}')">Submit</button>
+            ${allowsTabInstructions ? '<button class="btn btn-secondary" disabled data-tooltip="Coming soon">Add instructions</button>' : ''}
           </div>
         </div>
-      `).join('');
+      `;
     }
 
+    function renderQuestionPrompt(p) {
+      const json = p.json;
+      const header = json.header || '';
+      const question = json.question || p.text;
+      const options = json.options || [];
+      const multiSelect = json.multi_select || false;
+      const allowsOther = json.allows_other || false;
+      const inputType = multiSelect ? 'checkbox' : 'radio';
+
+      const optionsHtml = options.map((opt, idx) => `
+        <label class="prompt-option" onclick="selectOption('${p.id}', ${idx})">
+          <input type="${inputType}" name="prompt-${p.id}" value="${escapeHtml(opt)}">
+          <span class="prompt-option-label">${escapeHtml(opt)}</span>
+        </label>
+      `).join('');
+
+      const otherHtml = allowsOther ? `
+        <label class="prompt-option">
+          <input type="${inputType}" name="prompt-${p.id}" value="__other__" onclick="enableOtherInput('${p.id}')">
+          <span class="prompt-option-label">Other</span>
+        </label>
+        <input type="text" class="prompt-other-input" id="other-${p.id}" placeholder="Enter your answer..." disabled>
+      ` : '';
+
+      return `
+        <div class="prompt" data-prompt="${p.id}">
+          ${header ? `<div class="prompt-header">${escapeHtml(header)}</div>` : ''}
+          <div class="prompt-question">${escapeHtml(question)}</div>
+          <div class="prompt-options">
+            ${optionsHtml}
+            ${otherHtml}
+          </div>
+          <div class="prompt-actions">
+            <button class="btn btn-submit" onclick="submitRichPrompt('${p.id}')">Submit</button>
+          </div>
+        </div>
+      `;
+    }
+
+    function renderExitPlanPrompt(p) {
+      const json = p.json;
+      const options = json.options || [];
+
+      const optionsHtml = options.map((opt, idx) => `
+        <label class="prompt-option" onclick="selectOption('${p.id}', ${idx})">
+          <input type="radio" name="prompt-${p.id}" value="${escapeHtml(opt)}">
+          <span class="prompt-option-label">${escapeHtml(opt)}</span>
+        </label>
+      `).join('');
+
+      return `
+        <div class="prompt" data-prompt="${p.id}">
+          <div class="prompt-header">Plan Complete</div>
+          <div class="prompt-question">${escapeHtml(p.text)}</div>
+          <div class="prompt-options">
+            ${optionsHtml}
+          </div>
+          <div class="prompt-actions">
+            <button class="btn btn-submit" onclick="submitRichPrompt('${p.id}')">Submit</button>
+          </div>
+        </div>
+      `;
+    }
+
+    window.selectOption = (_promptId, _optionIdx) => {
+      // Radio buttons and checkboxes handle their own state
+      // This function is just for accessibility/mobile tap handling
+    };
+
+    window.enableOtherInput = (promptId) => {
+      const input = document.getElementById(`other-${promptId}`);
+      if (input) {
+        input.disabled = false;
+        input.focus();
+      }
+    };
+
+    window.submitRichPrompt = async (promptId) => {
+      promptId = Number(promptId);
+      const prompt = state.prompts.get(promptId);
+      if (!prompt || !prompt.json) {
+        console.error('Invalid prompt');
+        return;
+      }
+
+      const json = prompt.json;
+      let response;
+
+      if (json.prompt_type === 'permission') {
+        // Get selected radio button
+        const selected = document.querySelector(`input[name="prompt-${promptId}"]:checked`);
+        if (!selected) {
+          console.error('No option selected');
+          return;
+        }
+        response = {
+          type: 'option',
+          value: selected.value,
+        };
+      } else if (json.prompt_type === 'question') {
+        if (json.multi_select) {
+          // Get all checked checkboxes
+          const checked = Array.from(document.querySelectorAll(`input[name="prompt-${promptId}"]:checked`));
+          if (checked.length === 0) {
+            console.error('No options selected');
+            return;
+          }
+          const values = checked.map(el => {
+            if (el.value === '__other__') {
+              const otherInput = document.getElementById(`other-${promptId}`);
+              return otherInput ? otherInput.value : '';
+            }
+            return el.value;
+          });
+          response = {
+            type: 'text',
+            value: values.join(', '),
+          };
+        } else {
+          // Get selected radio button
+          const selected = document.querySelector(`input[name="prompt-${promptId}"]:checked`);
+          if (!selected) {
+            console.error('No option selected');
+            return;
+          }
+          if (selected.value === '__other__') {
+            const otherInput = document.getElementById(`other-${promptId}`);
+            if (!otherInput || !otherInput.value) {
+              console.error('Please enter a value for "Other"');
+              return;
+            }
+            response = {
+              type: 'text',
+              value: otherInput.value,
+            };
+          } else {
+            response = {
+              type: 'text',
+              value: selected.value,
+            };
+          }
+        }
+      } else if (json.prompt_type === 'exit_plan') {
+        // Get selected radio button
+        const selected = document.querySelector(`input[name="prompt-${promptId}"]:checked`);
+        if (!selected) {
+          console.error('No option selected');
+          return;
+        }
+        response = {
+          type: 'text',
+          value: selected.value,
+        };
+      }
+
+      try {
+        const res = await fetch(`/api/prompts/${promptId}/answer`, {
+          method: 'POST',
+          headers: {
+            'Content-Type': 'application/json',
+          },
+          body: JSON.stringify(response),
+        });
+        if (!res.ok) {
+          console.error('Failed to submit prompt response:', await res.text());
+        }
+      } catch (error) {
+        console.error('Error submitting prompt response:', error);
+      }
+    };
+
     window.respondToPrompt = async (promptId, action) => {
       promptId = Number(promptId);
       try {