diff --git a/quill_test.go b/quill_test.go
index cbbb9a2..2032823 100644
--- a/quill_test.go
+++ b/quill_test.go
@@ -2,6 +2,7 @@ package main
 
 import (
 	"context"
+	"fmt"
 	"net/http"
 	"net/http/httptest"
 	"strings"
@@ -95,3 +96,119 @@ func TestQuillNotInNestCrows(t *testing.T) {
 		t.Fatal("Quill must not need or earn a worker trust record")
 	}
 }
+
+func TestQuillPromptContainsNestHistory(t *testing.T) {
+	ts, _, qb := newQuillServer(t, "Hugin finished the build already.")
+	id := newNest(t, ts, "Lab", `"Hugin","Munin"`)
+
+	// 1. owner says something that sets up context
+	code, out := post(t, ts.URL+"/api/nests/"+id+"/messages",
+		`{"author":"owner","to":"Hugin","kind":"say","text":"build the widget factory"}`)
+	if code != http.StatusCreated {
+		t.Fatalf("post say: %d", code)
+	}
+	sayMsgID := out["msg_id"].(string)
+
+	// 2. Hugin delivers an answer
+	code, _ = post(t, ts.URL+"/api/nests/"+id+"/messages",
+		`{"author":"Hugin","kind":"deliver","text":"the widget factory is live","refers_to":"`+sayMsgID+`"}`)
+	if code != http.StatusCreated {
+		t.Fatalf("post deliver: %d", code)
+	}
+
+	// 3. owner asks Quill for status
+	code, _ = post(t, ts.URL+"/api/nests/"+id+"/messages",
+		`{"author":"owner","to":"Quill","kind":"request","text":"where did that get to"}`)
+	if code != http.StatusCreated {
+		t.Fatalf("post request to Quill: %d", code)
+	}
+
+	// Wait for Quill's reply (3 prior + 1 Quill reply = 4)
+	msgs := awaitMessages(t, ts, id, 4)
+	var quillReply map[string]any
+	for _, m := range msgs {
+		if m["author"] == "Quill" {
+			quillReply = m
+		}
+	}
+	if quillReply == nil {
+		t.Fatalf("Quill never answered: %v", msgs)
+	}
+
+	qb.mu.Lock()
+	defer qb.mu.Unlock()
+	if len(qb.pairs) != 1 {
+		t.Fatalf("want exactly one model call, got %d", len(qb.pairs))
+	}
+	prompt := qb.pairs[0][1]
+	if !strings.Contains(prompt, "build the widget factory") {
+		t.Fatalf("prompt must contain the owner's earlier message: %q", prompt)
+	}
+	if !strings.Contains(prompt, "the widget factory is live") {
+		t.Fatalf("prompt must contain Hugin's deliver: %q", prompt)
+	}
+}
+
+func TestQuillEmptyNestSaysQuiet(t *testing.T) {
+	ts, _, qb := newQuillServer(t, "All quiet here.")
+	id := newNest(t, ts, "Quiet", `"Hugin"`)
+
+	// Only message is the request to Quill — history excluding it is empty
+	code, _ := post(t, ts.URL+"/api/nests/"+id+"/messages",
+		`{"author":"owner","to":"Quill","kind":"request","text":"any updates?"}`)
+	if code != http.StatusCreated {
+		t.Fatalf("post: %d", code)
+	}
+	awaitMessages(t, ts, id, 2)
+
+	qb.mu.Lock()
+	defer qb.mu.Unlock()
+	if len(qb.pairs) != 1 {
+		t.Fatalf("want exactly one model call, got %d", len(qb.pairs))
+	}
+	prompt := qb.pairs[0][1]
+	if !strings.Contains(prompt, "no earlier messages") {
+		t.Fatalf("prompt must state the nest is empty: %q", prompt)
+	}
+}
+
+func TestQuillHistoryCap(t *testing.T) {
+	ts, _, qb := newQuillServer(t, "got it")
+	id := newNest(t, ts, "Busy", `"Hugin"`)
+
+	// Post 25 filler messages from owner
+	for i := 0; i < 25; i++ {
+		code, _ := post(t, ts.URL+"/api/nests/"+id+"/messages",
+			fmt.Sprintf(`{"author":"owner","kind":"say","text":"filler line %d"}`, i))
+		if code != http.StatusCreated {
+			t.Fatalf("post filler %d: %d", i, code)
+		}
+	}
+
+	// Ask Quill
+	code, _ := post(t, ts.URL+"/api/nests/"+id+"/messages",
+		`{"author":"owner","to":"Quill","kind":"request","text":"status"}`)
+	if code != http.StatusCreated {
+		t.Fatalf("post to Quill: %d", code)
+	}
+	awaitMessages(t, ts, id, 27)
+
+	qb.mu.Lock()
+	defer qb.mu.Unlock()
+	if len(qb.pairs) != 1 {
+		t.Fatalf("want exactly one model call, got %d", len(qb.pairs))
+	}
+	prompt := qb.pairs[0][1]
+	historyLines := 0
+	for _, line := range strings.Split(prompt, "\n") {
+		if strings.HasPrefix(line, "[") {
+			historyLines++
+		}
+	}
+	if historyLines > 20 {
+		t.Fatalf("history lines must be capped at 20, got %d\nprompt:\n%s", historyLines, prompt)
+	}
+	if historyLines == 0 {
+		t.Fatalf("expected some history lines, got none")
+	}
+}