diff --git a/crates/g3-core/src/prompts.rs b/crates/g3-core/src/prompts.rs
index de3fb68..2d243d7 100644
--- a/crates/g3-core/src/prompts.rs
+++ b/crates/g3-core/src/prompts.rs
@@ -49,10 +49,10 @@ Each plan item MUST have:
 - `description`: What will be done
 - `state`: todo | doing | done | blocked
 - `touches`: Paths/modules this affects (forces \"where does this live?\")
-- `checks`: Three required perspectives:
+- `checks`: Required test perspectives:
   - `happy`: {desc, target} - Normal successful operation
-  - `negative`: {desc, target} - Error handling, invalid input
-  - `boundary`: {desc, target} - Edge cases, limits
+  - `negative`: [{desc, target}, ...] - Error handling, invalid input (>=1 required)
+  - `boundary`: [{desc, target}, ...] - Edge cases, limits (>=1 required)
 - `evidence`: (required when done) File:line refs, test names
 - `notes`: (required when done) Short implementation explanation
 
@@ -79,11 +79,15 @@ When updating a plan:
       desc: \"Valid CSV imports 3 comics\"
       target: \"import::csv\"
     negative:
-      desc: \"Missing column errors with MissingColumn\"
-      target: \"import::csv\"
+      - desc: \"Missing column errors with MissingColumn\"
+        target: \"import::csv\"
+      - desc: \"Malformed row errors with ParseError\"
+        target: \"import::csv\"
     boundary:
-      desc: \"Empty file yields empty import without error\"
-      target: \"import::csv\"
+      - desc: \"Empty file yields empty import without error\"
+        target: \"import::csv\"
+      - desc: \"File with only headers yields empty import\"
+        target: \"import::csv\"
 ```
 
 When done, add evidence and notes:
@@ -306,7 +310,7 @@ Short description for providers without native calling specs:
 
 - **plan_write**: Create or update the Plan with YAML content
   - Format: {\"tool\": \"plan_write\", \"args\": {\"plan\": \"plan_id: my-plan\\nitems: [...]\"}}
-  - Example: {\"tool\": \"plan_write\", \"args\": {\"plan\": \"plan_id: feature-x\\nitems:\\n  - id: I1\\n    description: Add feature\\n    state: todo\\n    touches: [src/lib.rs]\\n    checks:\\n      happy: {desc: Works, target: lib}\\n      negative: {desc: Errors, target: lib}\\n      boundary: {desc: Edge, target: lib}\"}}
+  - Example: {\"tool\": \"plan_write\", \"args\": {\"plan\": \"plan_id: feature-x\\nitems:\\n  - id: I1\\n    description: Add feature\\n    state: todo\\n    touches: [src/lib.rs]\\n    checks:\\n      happy: {desc: Works, target: lib}\\n      negative:\\n        - {desc: Errors, target: lib}\\n      boundary:\\n        - {desc: Edge, target: lib}\"}}
 
 - **plan_approve**: Approve the current plan revision (called by user)
   - Format: {\"tool\": \"plan_approve\", \"args\": {}}
diff --git a/crates/g3-core/src/tool_definitions.rs b/crates/g3-core/src/tool_definitions.rs
index be581ba..d032361 100644
--- a/crates/g3-core/src/tool_definitions.rs
+++ b/crates/g3-core/src/tool_definitions.rs
@@ -289,14 +289,14 @@ fn create_core_tools(exclude_research: bool) -> Vec<Tool> {
   - touches: Array of paths/modules affected
   - checks:
       happy: {desc, target} - Normal successful operation
-      negative: {desc, target} - Error handling, invalid input
-      boundary: {desc, target} - Edge cases, limits
+      negative: [{desc, target}, ...] - Error handling, invalid input (>=1 required)
+      boundary: [{desc, target}, ...] - Edge cases, limits (>=1 required)
   - evidence: Array of file:line refs, test names (required when done)
   - notes: Implementation explanation (required when done)
 
 Rules:
 - Keep items ≤ 7 by default
-- All three checks (happy, negative, boundary) are required
+- All checks required: 1 happy, 1+ negative, 1+ boundary
 - Cannot remove items from an approved plan (mark as blocked instead)
 - Evidence and notes required when marking item as done"#.to_string(),
         input_schema: json!({
diff --git a/crates/g3-core/src/tools/plan.rs b/crates/g3-core/src/tools/plan.rs
index 4d77b1b..75cc73d 100644
--- a/crates/g3-core/src/tools/plan.rs
+++ b/crates/g3-core/src/tools/plan.rs
@@ -96,18 +96,30 @@ impl Check {
 pub struct Checks {
     /// Happy path check - normal successful operation
     pub happy: Check,
-    /// Negative case check - error handling, invalid input
-    pub negative: Check,
-    /// Boundary condition check - edge cases, limits
-    pub boundary: Check,
+    /// Negative case checks - error handling, invalid input (at least 1 required)
+    pub negative: Vec<Check>,
+    /// Boundary condition checks - edge cases, limits (at least 1 required)
+    pub boundary: Vec<Check>,
 }
 
 impl Checks {
-    /// Validate all three checks.
+    /// Validate all checks (1 happy, 1+ negative, 1+ boundary).
     pub fn validate(&self) -> Result<()> {
         self.happy.validate().map_err(|e| anyhow!("happy check: {}", e))?;
-        self.negative.validate().map_err(|e| anyhow!("negative check: {}", e))?;
-        self.boundary.validate().map_err(|e| anyhow!("boundary check: {}", e))?;
+        
+        if self.negative.is_empty() {
+            return Err(anyhow!("at least one negative check is required"));
+        }
+        for (i, check) in self.negative.iter().enumerate() {
+            check.validate().map_err(|e| anyhow!("negative check [{}]: {}", i, e))?;
+        }
+        
+        if self.boundary.is_empty() {
+            return Err(anyhow!("at least one boundary check is required"));
+        }
+        for (i, check) in self.boundary.iter().enumerate() {
+            check.validate().map_err(|e| anyhow!("boundary check [{}]: {}", i, e))?;
+        }
         Ok(())
     }
 }
@@ -927,8 +939,8 @@ mod tests {
     fn make_test_checks() -> Checks {
         Checks {
             happy: make_test_check(),
-            negative: make_test_check(),
-            boundary: make_test_check(),
+            negative: vec![make_test_check()],
+            boundary: vec![make_test_check()],
         }
     }
 
@@ -969,6 +981,55 @@ mod tests {
         assert!(empty_target.validate().is_err());
     }
 
+    #[test]
+    fn test_checks_validation_multiple_negative_and_boundary() {
+        // Multiple negative and boundary checks should validate
+        let checks = Checks {
+            happy: make_test_check(),
+            negative: vec![
+                Check::new("Invalid input", "parse::input"),
+                Check::new("Missing file", "io::read"),
+                Check::new("Network error", "net::connect"),
+            ],
+            boundary: vec![
+                Check::new("Empty input", "parse::input"),
+                Check::new("Max size input", "parse::input"),
+            ],
+        };
+        assert!(checks.validate().is_ok());
+    }
+
+    #[test]
+    fn test_checks_validation_empty_negative_fails() {
+        let checks = Checks {
+            happy: make_test_check(),
+            negative: vec![],  // Empty - should fail
+            boundary: vec![make_test_check()],
+        };
+        let err = checks.validate().unwrap_err();
+        assert!(err.to_string().contains("at least one negative check"));
+    }
+
+    #[test]
+    fn test_checks_validation_empty_boundary_fails() {
+        let checks = Checks {
+            happy: make_test_check(),
+            negative: vec![make_test_check()],
+            boundary: vec![],  // Empty - should fail
+        };
+        let err = checks.validate().unwrap_err();
+        assert!(err.to_string().contains("at least one boundary check"));
+    }
+
+    #[test]
+    fn test_checks_validation_single_of_each_passes() {
+        // Minimum case: exactly 1 of each
+        let checks = make_test_checks();
+        assert!(checks.validate().is_ok());
+        assert_eq!(checks.negative.len(), 1);
+        assert_eq!(checks.boundary.len(), 1);
+    }
+
     #[test]
     fn test_plan_item_validation() {
         let item = make_test_item("I1");