feat: add feasability criteria

apps/api/src/planproof_api/agent/planner.py

@@ -23,6 +23,10 @@
     "If the user did not specify a duration, ask about it in questions. "
     "Every task MUST have a duration of at least 5 minutes. You are forbidden "
     "from creating zero-duration tasks to fit constraints. "
+    "If a task duration is not specified, assume a minimum of 25 minutes for "
+    "anything labeled \"Meeting\" and 15 minutes for chores. You are "
+    "FORBIDDEN from scheduling tasks shorter than 15 minutes unless the user "
+    "explicitly asks for a \"quick check\" or \"5-min task\". "
     "Current time is provided in 12h format. Be extremely careful with AM/PM: "
     "3:15 PM is 15:15. If the current time is 6 AM, a 3 PM meeting is in the "
     "future and must be scheduled. "

apps/api/src/planproof_api/routes.py

@@ -151,10 +151,11 @@ def _validate_plan(
         plan, metadata.actionable_tasks
     )
     missing_keywords = _missing_keywords(plan, metadata.actionable_tasks)
-    human_feasibility_flags = check_feasibility(plan)
+    human_feasibility_flags, feasibility_errors = check_feasibility(plan)
     zero_duration_flags = 0
 
     errors: list[str] = list(constraint_errors)
+    errors.extend(feasibility_errors)
     current_dt = isoparse(current_time)
     for item in plan:
         start_dt = isoparse(item.start_time)
@@ -254,6 +255,11 @@ def _repair_plan(
         "RULE 2: Do not delete tasks to fix overlaps. Shorten them instead "
         "(e.g., change 60m to 15m)."
     )
+    repair_prompt = (
+        f"{repair_prompt}\n\n"
+        "Your previous attempt used unrealistic 5-minute durations. Increase "
+        "durations to at least 25 minutes and shift other tasks accordingly."
+    )
     if constraint_violation_count > 0:
         repair_prompt = (
             f"{repair_prompt}\n\n"

apps/api/tests/test_feasibility.py

@@ -21,13 +21,15 @@ def test_check_feasibility_no_long_blocks() -> None:
         _item("2025-01-18T11:15:00-05:00", "2025-01-18T13:00:00-05:00"),
     ]
 
-    assert check_feasibility(items) == 0
+    flags, _ = check_feasibility(items)
+    assert flags == 0
 
 
 def test_check_feasibility_single_block_over_limit() -> None:
     items = [_item("2025-01-18T09:00:00-05:00", "2025-01-18T13:30:00-05:00")]
 
-    assert check_feasibility(items) == 1
+    flags, _ = check_feasibility(items)
+    assert flags == 1
 
 
 def test_check_feasibility_multiple_blocks_over_limit() -> None:
@@ -36,7 +38,8 @@ def test_check_feasibility_multiple_blocks_over_limit() -> None:
         _item("2025-01-18T13:45:00-05:00", "2025-01-18T18:15:00-05:00"),
     ]
 
-    assert check_feasibility(items) == 2
+    flags, _ = check_feasibility(items)
+    assert flags == 2
 
 
 def test_check_feasibility_break_exactly_15_minutes() -> None:
@@ -45,7 +48,8 @@ def test_check_feasibility_break_exactly_15_minutes() -> None:
         _item("2025-01-18T13:15:00-05:00", "2025-01-18T15:00:00-05:00"),
     ]
 
-    assert check_feasibility(items) == 0
+    flags, _ = check_feasibility(items)
+    assert flags == 0
 
 
 def test_check_feasibility_overlapping_tasks() -> None:
@@ -54,4 +58,22 @@ def test_check_feasibility_overlapping_tasks() -> None:
         _item("2025-01-18T10:30:00-05:00", "2025-01-18T15:30:00-05:00"),
     ]
 
-    assert check_feasibility(items) == 1
+    flags, _ = check_feasibility(items)
+    assert flags == 1
+
+
+def test_check_feasibility_short_meeting() -> None:
+    items = [
+        PlanItem(
+            task="Team Meeting",
+            start_time="2025-01-18T09:00:00-05:00",
+            end_time="2025-01-18T09:10:00-05:00",
+            timebox_minutes=0,
+            why="Test",
+        )
+    ]
+
+    flags, errors = check_feasibility(items)
+
+    assert flags == 1
+    assert "Meeting duration is realistically too short." in errors

eval/feasibility.py

@@ -8,14 +8,15 @@
     from planproof_api.agent.schemas import PlanItem
 
 
-def check_feasibility(plan_items: List["PlanItem"]) -> int:
+def check_feasibility(plan_items: List["PlanItem"]) -> tuple[int, list[str]]:
     if not plan_items:
-        return 0
+        return 0, []
 
     items = sorted(plan_items, key=lambda item: isoparse(item.start_time))
     block_start = isoparse(items[0].start_time)
     block_end = isoparse(items[0].end_time)
     flags = 0
+    errors: list[str] = []
 
     for item in items[1:]:
         start_time = isoparse(item.start_time)
@@ -32,8 +33,18 @@ def check_feasibility(plan_items: List["PlanItem"]) -> int:
             if end_time > block_end:
                 block_end = end_time
 
+    for item in items:
+        label = (item.task or "").lower()
+        if "meeting" in label or "sync" in label:
+            start_time = isoparse(item.start_time)
+            end_time = isoparse(item.end_time)
+            duration_minutes = (end_time - start_time).total_seconds() / 60
+            if duration_minutes < 20:
+                flags += 1
+                errors.append("Meeting duration is realistically too short.")
+
     block_minutes = (block_end - block_start).total_seconds() / 60
     if block_minutes > 240:
         flags += 1
 
-    return flags
+    return flags, errors