diff --git a/get-shit-done/references/questioning.md b/get-shit-done/references/questioning.md
index 79a7e4ce6..14a03db38 100644
--- a/get-shit-done/references/questioning.md
+++ b/get-shit-done/references/questioning.md
@@ -100,6 +100,23 @@ Users who want a slightly modified version of an option can select "Other" and r
 
 </using_askuserquestion>
 
+<freeform_rule>
+
+**When the user wants to explain freely, STOP using AskUserQuestion.**
+
+If a user selects "Other" and their response signals they want to describe something in their own words (e.g., "let me describe it", "I'll explain", "something else", or any open-ended reply that isn't choosing/modifying an existing option), you MUST:
+
+1. **Ask your follow-up as plain text** — NOT via AskUserQuestion
+2. **Wait for them to type at the normal prompt**
+3. **Resume AskUserQuestion** only after processing their freeform response
+
+The same applies if YOU include a freeform-indicating option (like "Let me explain" or "Describe in detail") and the user selects it.
+
+**Wrong:** User says "let me describe it" → AskUserQuestion("What feature?", ["Feature A", "Feature B", "Describe in detail"])
+**Right:** User says "let me describe it" → "Go ahead — what are you thinking?"
+
+</freeform_rule>
+
 <context_checklist>
 
 Use this as a **background checklist**, not a conversation structure. Check these mentally as you go. If gaps remain, weave questions naturally.
diff --git a/get-shit-done/workflows/discuss-phase.md b/get-shit-done/workflows/discuss-phase.md
index df4d546db..d5fb5a67c 100644
--- a/get-shit-done/workflows/discuss-phase.md
+++ b/get-shit-done/workflows/discuss-phase.md
@@ -422,7 +422,7 @@ Ask 4 questions per area before offering to continue or move on. Each answer oft
 **Question design:**
 - Options should be concrete, not abstract ("Cards" not "Option A")
 - Each answer should inform the next question
-- If user picks "Other", receive their input, reflect it back, confirm
+- If user picks "Other" to provide freeform input (e.g., "let me describe it", "something else", or an open-ended reply), ask your follow-up as plain text — NOT another AskUserQuestion. Wait for them to type at the normal prompt, then reflect their input back and confirm before resuming AskUserQuestion for the next question.
 
 **Scope creep handling:**
 If user mentions something outside the phase domain:
diff --git a/get-shit-done/workflows/new-milestone.md b/get-shit-done/workflows/new-milestone.md
index 252694ae4..758ad74f6 100644
--- a/get-shit-done/workflows/new-milestone.md
+++ b/get-shit-done/workflows/new-milestone.md
@@ -27,8 +27,9 @@ Read all files referenced by the invoking prompt's execution_context before star
 
 **If no context file:**
 - Present what shipped in last milestone
-- Ask: "What do you want to build next?"
-- Use AskUserQuestion to explore features, priorities, constraints, scope
+- Ask inline (freeform, NOT AskUserQuestion): "What do you want to build next?"
+- Wait for their response, then use AskUserQuestion to probe specifics
+- If user selects "Other" at any point to provide freeform input, ask follow-up as plain text — not another AskUserQuestion
 
 ## 3. Determine Milestone Version