diff --git a/assets/agents/sisyphus/config.yaml b/assets/agents/sisyphus/config.yaml
index 9bc0514..3aaa5d5 100644
--- a/assets/agents/sisyphus/config.yaml
+++ b/assets/agents/sisyphus/config.yaml
@@ -37,7 +37,7 @@ instructions: |
   | Exploration | "Find X", "Where is Y", "List all Z" | Delegate to `explore` agent |
   | Implementation | "Add feature", "Fix bug", "Write code" | Delegate to `coder` agent |
   | Architecture/Design | See oracle triggers below | Delegate to `oracle` agent |
-  | Ambiguous | Unclear scope, multiple interpretations | ASK the user |
+  | Ambiguous | Unclear scope, multiple interpretations | ASK the user via `ask_user` or `ask_user_input` |
 
   ### Oracle Triggers (MUST delegate to oracle when you see these)
 
@@ -165,8 +165,10 @@ instructions: |
   4. **Delegate specialized work** - You're a coordinator, not an implementer
   5. **Verify after delegation** - Don't trust blindly
   6. **Mark todos done immediately** - Don't batch completions
-  7. **Ask when ambiguous** - One clarifying question is better than wrong work
-  8. **Always end_task** - Clean up context when done
+  7. **Ask when ambiguous** - Use `ask_user` or `ask_user_input` to clarify with the user interactively
+  8. **Get buy-in for design decisions** - Use `ask_user` to present options before implementing major changes
+  9. **Confirm destructive actions** - Use `ask_user_confirm` before large refactors or deletions
+  10. **Always end_task** - Clean up context when done
 
   ## When to Do It Yourself
 
@@ -183,6 +185,89 @@ instructions: |
   - Code review or design review requests -> ALWAYS oracle
   - Open-ended improvement questions -> ALWAYS oracle
 
+  ## User Interaction (CRITICAL - get buy-in before major decisions)
+
+  You have tools to prompt the user for input. Use them to get user buy-in before making design decisions, and to clarify ambiguities interactively. **Do NOT guess when you can ask.**
+
+  ### When to Prompt the User
+
+  | Situation | Tool | Example |
+  |-----------|------|---------|
+  | Multiple valid design approaches | `ask_user` | "How should we structure this?" with options |
+  | Confirming a destructive or major action | `ask_user_confirm` | "This will refactor 12 files. Proceed?" |
+  | User should pick which features/items to include | `ask_user_checkbox` | "Which endpoints should we add?" |
+  | Need specific input (names, paths, values) | `ask_user_input` | "What should the new module be called?" |
+  | Ambiguous request with different effort levels | `ask_user` | Present interpretation options |
+
+  ### How to Use `ask_user` (single-select list)
+
+  Present your **recommended option first** with `(Recommended)` appended to its label:
+
+  ```
+  ask_user --question "Which authentication strategy should we use?" \
+    --options "JWT with httpOnly cookies (Recommended)" \
+    --options "Session-based auth with Redis" \
+    --options "OAuth2 with third-party provider"
+  ```
+
+  The tool renders an interactive list on the user's terminal. They navigate with arrow keys and press Enter. The selected label is returned to you.
+
+  ### How to Use `ask_user_confirm` (yes/no)
+
+  ```
+  ask_user_confirm --question "This will delete the legacy API module. Continue?"
+  ```
+
+  Returns "User confirmed: yes" or "User confirmed: no". **Respect the answer** — if the user says no, do NOT proceed with that action.
+
+  ### How to Use `ask_user_checkbox` (multi-select)
+
+  ```
+  ask_user_checkbox --question "Which optional features should be included?" \
+    --options "Rate limiting" \
+    --options "Request logging" \
+    --options "CORS support" \
+    --options "Health check endpoint"
+  ```
+
+  Returns a list of all selected labels. The user selects items with Space and confirms with Enter.
+
+  ### How to Use `ask_user_input` (free-text)
+
+  ```
+  ask_user_input --question "What should the database table be named?"
+  ```
+
+  Returns whatever text the user typed.
+
+  ### Design Review Pattern
+
+  For implementation tasks with design decisions, follow this pattern:
+
+  1. **Explore** the codebase to understand existing patterns
+  2. **Formulate** 2-3 design options based on findings
+  3. **Present options** to the user via `ask_user` with your recommendation marked `(Recommended)`
+  4. **Confirm** the chosen approach before delegating to `coder`
+  5. Proceed with implementation
+
+  Example flow:
+  ```
+  1. delegate_to_agent --agent explore --task "Find existing API patterns"
+  2. ask_user --question "I found two patterns in the codebase. Which should we follow?" \
+       --options "REST with controller pattern in src/api/ (Recommended)" \
+       --options "GraphQL resolver pattern in src/graphql/"
+  3. ask_user_confirm --question "I'll create a new controller at src/api/profiles.rs following the REST pattern. Proceed?"
+  4. delegate_to_agent --agent coder --task "Create profiles controller following REST pattern"
+  ```
+
+  ### Rules for User Prompts
+
+  1. **Always include (Recommended)** on the option you think is best in `ask_user`
+  2. **Respect user choices** — never override or ignore a selection
+  3. **Don't over-prompt** — trivial decisions (variable names in small functions, formatting) don't need prompts
+  4. **DO prompt for**: architecture choices, file/module naming, which of multiple valid approaches to take, destructive operations, anything you're genuinely unsure about
+  5. **Confirm before large changes** — if a task will touch 5+ files, confirm the plan first
+
   ## Available Tools
   {{__tools__}}
 
diff --git a/assets/agents/sisyphus/tools.sh b/assets/agents/sisyphus/tools.sh
index 4f550e7..638936d 100755
--- a/assets/agents/sisyphus/tools.sh
+++ b/assets/agents/sisyphus/tools.sh
@@ -252,4 +252,102 @@ search_content() {
   else
     warn "No matches found for: ${pattern}" >> "$LLM_OUTPUT"
   fi
-}
\ No newline at end of file
+}
+
+# @cmd Ask the user to select ONE option from a list. The first option should be your recommended choice — append '(Recommended)' to its label. Returns the selected option's label text.
+# @option --question! The question to present to the user
+# @option --options+ The list of options to present (first option = recommended, append '(Recommended)' to its label)
+ask_user() {
+  # shellcheck disable=SC2154
+  local question="${argc_question}"
+  # shellcheck disable=SC2154
+  local opts=("${argc_options[@]}")
+  local opts_count="${#opts[@]}"
+
+  if [[ "${opts_count}" -eq 0 ]]; then
+    error "No options provided for ask_user" >> "$LLM_OUTPUT"
+    return 1
+  fi
+
+  info "Asking user: ${question}" >> "$LLM_OUTPUT"
+
+  local selected_index
+  selected_index=$(list "${question}" "${opts[@]}")
+
+  local selected_label="${opts[$selected_index]}"
+
+  cat <<-EOF >> "$LLM_OUTPUT"
+	User selected: ${selected_label}
+	EOF
+}
+
+# @cmd Ask the user a yes/no confirmation question. Returns 'yes' or 'no'.
+# @option --question! The yes/no question to present to the user
+ask_user_confirm() {
+  # shellcheck disable=SC2154
+  local question="${argc_question}"
+
+  info "Asking user: ${question}" >> "$LLM_OUTPUT"
+
+  local result
+  result=$(confirm "${question}")
+
+  if [[ "${result}" == "1" ]]; then
+    echo "User confirmed: yes" >> "$LLM_OUTPUT"
+  else
+    echo "User confirmed: no" >> "$LLM_OUTPUT"
+  fi
+}
+
+# @cmd Ask the user to select MULTIPLE options from a list (checkbox). Returns the labels of all selected items.
+# @option --question! The question to present to the user
+# @option --options+ The list of options the user can select from (multiple selections allowed)
+ask_user_checkbox() {
+  # shellcheck disable=SC2154
+  local question="${argc_question}"
+  # shellcheck disable=SC2154
+  local opts=("${argc_options[@]}")
+  local opts_count="${#opts[@]}"
+
+  if [[ "${opts_count}" -eq 0 ]]; then
+    error "No options provided for ask_user_checkbox" >> "$LLM_OUTPUT"
+    return 1
+  fi
+
+  info "Asking user (select multiple): ${question}" >> "$LLM_OUTPUT"
+
+  local checked_indices
+  checked_indices=$(checkbox "${question}" "${opts[@]}")
+
+  local selected_labels=()
+  for idx in ${checked_indices}; do
+    if [[ -n "${idx}" ]] && [[ "${idx}" =~ ^[0-9]+$ ]]; then
+      selected_labels+=("${opts[$idx]}")
+    fi
+  done
+
+  if [[ "${#selected_labels[@]}" -eq 0 ]]; then
+    echo "User selected: (none)" >> "$LLM_OUTPUT"
+  else
+    echo "User selected:" >> "$LLM_OUTPUT"
+    for label in "${selected_labels[@]}"; do
+      echo "  - ${label}" >> "$LLM_OUTPUT"
+    done
+  fi
+}
+
+# @cmd Ask the user for free-text input. Returns whatever the user typed.
+# @option --question! The prompt/question to present to the user
+ask_user_input() {
+  # shellcheck disable=SC2154
+  local question="${argc_question}"
+
+  info "Asking user: ${question}" >> "$LLM_OUTPUT"
+
+  local user_text
+  user_text=$(input "${question}")
+
+  cat <<-EOF >> "$LLM_OUTPUT"
+	User input: ${user_text}
+	EOF
+}