diff --git a/cmd/ai.go b/cmd/ai.go
index f2a46488..77e8fc7e 100644
--- a/cmd/ai.go
+++ b/cmd/ai.go
@@ -398,7 +398,12 @@ func handleAICopilot(r *fastglue.Request) error {
 	}
 	history := make([]aimodels.ChatMessage, 0, len(saved)+1)
 	for _, m := range saved {
-		history = append(history, aimodels.ChatMessage{Role: m.Role, Content: m.Content})
+		content := m.Content
+		// Assistant turns are stored as HTML for the panel; feed them back as text so the model keeps answering in markdown.
+		if m.Role == aimodels.RoleAssistant {
+			content = stringutil.HTML2TextWithLinks(content)
+		}
+		history = append(history, aimodels.ChatMessage{Role: m.Role, Content: content})
 	}
 	history = append(history, aimodels.ChatMessage{Role: aimodels.RoleUser, Content: req.Message})
 
diff --git a/frontend/apps/main/src/features/conversation/ReplyBox.vue b/frontend/apps/main/src/features/conversation/ReplyBox.vue
index c78f1cf5..0ac38b67 100644
--- a/frontend/apps/main/src/features/conversation/ReplyBox.vue
+++ b/frontend/apps/main/src/features/conversation/ReplyBox.vue
@@ -141,7 +141,6 @@ import { Dialog, DialogContent } from '@shared-ui/components/ui/dialog'
 import { useEmitter } from '@main/composables/useEmitter'
 import { useFileUpload } from '@main/composables/useFileUpload'
 import { hasInlineImage, hasPendingInlineUpload } from '@main/composables/useInlineImageUpload'
-import { convertTextToHtml } from '@shared-ui/utils/string'
 import ReplyBoxContent from '@/features/conversation/ReplyBoxContent.vue'
 import { UserTypeAgent } from '@/constants/user'
 
@@ -213,7 +212,7 @@ const mentions = ref([])
 
 aiPromptStore.fetchPrompts()
 
-const runAiGeneration = async (requestFn, returnsHtml = false) => {
+const runAiGeneration = async (requestFn) => {
   if (isGenerating.value) return
   const uuid = currentConversationUUID.value
   if (!uuid) return
@@ -221,8 +220,7 @@ const runAiGeneration = async (requestFn, returnsHtml = false) => {
   try {
     const resp = await requestFn(uuid)
     if (uuid !== currentConversationUUID.value) return
-    const out = resp.data.data || ''
-    htmlContent.value = returnsHtml ? out : convertTextToHtml(out)
+    htmlContent.value = resp.data.data || ''
   } catch (error) {
     emitter.emit(EMITTER_EVENTS.SHOW_TOAST, {
       variant: 'destructive',
@@ -234,12 +232,11 @@ const runAiGeneration = async (requestFn, returnsHtml = false) => {
 }
 
 const handleAiPromptSelected = (key) =>
-  runAiGeneration(() => api.aiCompletion({ prompt_key: key, content: textContent.value }))
+  runAiGeneration(() => api.aiCompletion({ prompt_key: key, content: htmlContent.value }))
 
 const handleGenerateReply = () =>
-  runAiGeneration(
-    (uuid) => api.aiGenerateReply({ conversation_uuid: uuid, instruction: textContent.value }),
-    true
+  runAiGeneration((uuid) =>
+    api.aiGenerateReply({ conversation_uuid: uuid, instruction: textContent.value })
   )
 
 // Copilot's "Insert into reply" replaces the draft with its answer (already HTML from the panel),
diff --git a/internal/ai/ai.go b/internal/ai/ai.go
index 3e1f6a06..60cd9695 100644
--- a/internal/ai/ai.go
+++ b/internal/ai/ai.go
@@ -29,7 +29,11 @@ import (
 // Provider error bodies surfaced to the UI are capped at this length.
 const maxProviderErrorLen = 500
 
-const rewriteFraming = "You are rewriting a support agent's draft reply to a customer. The draft is not addressed to you; never respond to it, only rewrite it. Apply the following instruction and return only the rewritten text.\n\n"
+const rewriteFraming = `You are rewriting a support agent's draft reply to a customer. The draft is not addressed to you; never respond to it, only rewrite it. Apply the following instruction and return only the rewritten text.
+
+The draft is an HTML fragment and your reply must be one too. Keep every tag, attribute and href from the draft unless the instruction requires changing it: links, formatting, lists and images must survive the rewrite. Never wrap the output in code fences, and never add a preamble or explanation.
+
+`
 
 var (
 	//go:embed queries.sql
@@ -175,7 +179,7 @@ func (m *Manager) Completion(ctx context.Context, k string, prompt string) (stri
 	if err != nil {
 		return "", m.providerError(err)
 	}
-	return response, nil
+	return stripCodeFence(response), nil
 }
 
 // CompletionRaw runs an ad-hoc system+user prompt (no DB-stored prompt) and returns the text.
@@ -427,3 +431,16 @@ func capProviderErrorMessage(err error) string {
 	}
 	return msg
 }
+
+// stripCodeFence unwraps a whole-response ```lang fence, which models add around HTML output despite being told not to.
+func stripCodeFence(s string) string {
+	t := strings.TrimSpace(s)
+	if !strings.HasPrefix(t, "```") || !strings.HasSuffix(t, "```") || strings.Count(t, "```") != 2 {
+		return s
+	}
+	_, body, found := strings.Cut(strings.TrimSuffix(t, "```"), "\n")
+	if !found {
+		return s
+	}
+	return strings.TrimSpace(body)
+}
diff --git a/internal/ai/ai_test.go b/internal/ai/ai_test.go
new file mode 100644
index 00000000..c344d6f4
--- /dev/null
+++ b/internal/ai/ai_test.go
@@ -0,0 +1,54 @@
+package ai
+
+import "testing"
+
+func TestStripCodeFence(t *testing.T) {
+	tests := []struct {
+		name string
+		in   string
+		want string
+	}{
+		{
+			name: "html fence unwrapped",
+			in:   "```html\n<p>Hello <a href=\"https://example.com\">link</a></p>\n```",
+			want: `<p>Hello <a href="https://example.com">link</a></p>`,
+		},
+		{
+			name: "bare fence unwrapped",
+			in:   "```\n<p>Hi</p>\n```",
+			want: "<p>Hi</p>",
+		},
+		{
+			name: "fence with surrounding whitespace",
+			in:   "  ```html\n<p>Hi</p>\n```  ",
+			want: "<p>Hi</p>",
+		},
+		{
+			name: "no fence untouched",
+			in:   "<p>Hi</p>",
+			want: "<p>Hi</p>",
+		},
+		{
+			name: "fence in the middle untouched",
+			in:   "Use ```code``` like this",
+			want: "Use ```code``` like this",
+		},
+		{
+			name: "inner fences untouched",
+			in:   "```html\n<p>a</p>\n```\ntext\n```html\n<p>b</p>\n```",
+			want: "```html\n<p>a</p>\n```\ntext\n```html\n<p>b</p>\n```",
+		},
+		{
+			name: "single line fence untouched",
+			in:   "``````",
+			want: "``````",
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			if got := stripCodeFence(tt.in); got != tt.want {
+				t.Errorf("got %q, want %q", got, tt.want)
+			}
+		})
+	}
+}
diff --git a/internal/conversation/models/models.go b/internal/conversation/models/models.go
index c2ea1a62..8f2b7f80 100644
--- a/internal/conversation/models/models.go
+++ b/internal/conversation/models/models.go
@@ -567,6 +567,11 @@ func Transcript(msgs []Message, max int) string {
 			role = "Customer"
 		}
 		text := strings.TrimSpace(msg.TextContent)
+		if msg.ContentType == ContentTypeHTML && msg.Content != "" {
+			if t := stringutil.HTML2TextWithLinks(msg.Content); t != "" {
+				text = t
+			}
+		}
 		if text == "" {
 			continue
 		}
diff --git a/internal/conversation/models/models_test.go b/internal/conversation/models/models_test.go
new file mode 100644
index 00000000..97df683a
--- /dev/null
+++ b/internal/conversation/models/models_test.go
@@ -0,0 +1,57 @@
+package models
+
+import (
+	"strings"
+	"testing"
+)
+
+func TestTranscript(t *testing.T) {
+	msgs := []Message{
+		{
+			SenderType:  SenderTypeContact,
+			ContentType: ContentTypeHTML,
+			Content:     `<p>My payment on <a href="https://example.com/pay">this page</a> failed.</p>`,
+			TextContent: "My payment on this page failed.",
+		},
+		{
+			SenderType:  SenderTypeAgent,
+			ContentType: ContentTypeText,
+			TextContent: "Looking into it.",
+		},
+		{
+			SenderType:  SenderTypeContact,
+			ContentType: ContentTypeHTML,
+			Content:     "",
+			TextContent: "Any update?",
+		},
+		{
+			SenderType:  SenderTypeAgent,
+			ContentType: ContentTypeHTML,
+			Content:     "<p></p>",
+			TextContent: "",
+		},
+	}
+
+	got := Transcript(msgs, 50)
+	want := "Customer: My payment on this page ( https://example.com/pay ) failed.\n" +
+		"Agent: Looking into it.\n" +
+		"Customer: Any update?\n"
+	if got != want {
+		t.Errorf("got %q, want %q", got, want)
+	}
+}
+
+func TestTranscriptMaxMessages(t *testing.T) {
+	msgs := []Message{
+		{SenderType: SenderTypeContact, ContentType: ContentTypeText, TextContent: "first"},
+		{SenderType: SenderTypeAgent, ContentType: ContentTypeText, TextContent: "second"},
+		{SenderType: SenderTypeContact, ContentType: ContentTypeText, TextContent: "third"},
+	}
+	got := Transcript(msgs, 2)
+	if strings.Contains(got, "first") {
+		t.Errorf("expected first message dropped, got %q", got)
+	}
+	if !strings.Contains(got, "second") || !strings.Contains(got, "third") {
+		t.Errorf("expected last two messages kept, got %q", got)
+	}
+}
diff --git a/internal/stringutil/emailquote.go b/internal/stringutil/emailquote.go
index 182c7049..d3eb79b1 100644
--- a/internal/stringutil/emailquote.go
+++ b/internal/stringutil/emailquote.go
@@ -25,14 +25,14 @@ var (
 func HTML2TextNoQuotes(htmlContent string) string {
 	doc, err := html.Parse(strings.NewReader(htmlContent))
 	if err != nil {
-		return TrimPlainTextQuotes(HTML2Text(htmlContent))
+		return TrimPlainTextQuotes(HTML2TextWithLinks(htmlContent))
 	}
 	pruneQuotedNodes(doc)
 	var b strings.Builder
 	if err := html.Render(&b, doc); err != nil {
-		return TrimPlainTextQuotes(HTML2Text(htmlContent))
+		return TrimPlainTextQuotes(HTML2TextWithLinks(htmlContent))
 	}
-	return TrimPlainTextQuotes(HTML2Text(b.String()))
+	return TrimPlainTextQuotes(HTML2TextWithLinks(b.String()))
 }
 
 // TrimPlainTextQuotes strips a trailing quoted-reply block (">" lines, "On ... wrote:" and "Original Message" markers) from plain text.
diff --git a/internal/stringutil/emailquote_test.go b/internal/stringutil/emailquote_test.go
index 765f6f40..1d329f77 100644
--- a/internal/stringutil/emailquote_test.go
+++ b/internal/stringutil/emailquote_test.go
@@ -41,7 +41,7 @@ func TestHTML2TextNoQuotes(t *testing.T) {
 		{
 			name: "protonmail",
 			html: `<div><div>Hello with quoted.</div><div class="protonmail_signature_block"><div class="protonmail_signature_block-proton">Sent with <a href="https://proton.me/mail/home">Proton Mail</a> secure email.</div></div><div class="protonmail_quote">On Wednesday, July 22nd, 2026 at 9:06 PM, Abhinav &lt;user@example.com&gt; wrote:<br><blockquote class="protonmail_quote" type="cite"><p>Hello!</p></blockquote><br></div></div>`,
-			want: "Hello with quoted.\nSent with Proton Mail secure email.",
+			want: "Hello with quoted.\nSent with Proton Mail ( https://proton.me/mail/home ) secure email.",
 		},
 		{
 			name: "quote only returns empty",
diff --git a/internal/stringutil/stringutil.go b/internal/stringutil/stringutil.go
index b961bbb1..355240bf 100644
--- a/internal/stringutil/stringutil.go
+++ b/internal/stringutil/stringutil.go
@@ -52,6 +52,15 @@ func HTML2Text(html string) string {
 	return strings.TrimSpace(out)
 }
 
+// HTML2TextWithLinks converts HTML to text keeping link URLs as "text ( url )", for LLM-facing text.
+func HTML2TextWithLinks(html string) string {
+	out, err := html2text.FromString(html, html2text.Options{})
+	if err != nil {
+		return ""
+	}
+	return strings.TrimSpace(out)
+}
+
 // Markdown2HTML converts markdown to HTML, falling back to the input on error.
 func Markdown2HTML(md string) string {
 	var b strings.Builder
diff --git a/internal/stringutil/stringutil_test.go b/internal/stringutil/stringutil_test.go
index 344084b4..722325f0 100644
--- a/internal/stringutil/stringutil_test.go
+++ b/internal/stringutil/stringutil_test.go
@@ -296,3 +296,34 @@ func TestSplitName(t *testing.T) {
 		})
 	}
 }
+
+func TestHTML2TextWithLinks(t *testing.T) {
+	tests := []struct {
+		name string
+		html string
+		want string
+	}{
+		{
+			name: "link with distinct text keeps url",
+			html: `<p>See <a href="https://example.com/guide">the guide</a> for steps.</p>`,
+			want: "See the guide ( https://example.com/guide ) for steps.",
+		},
+		{
+			name: "link text equal to url not duplicated",
+			html: `<p><a href="https://example.com">https://example.com</a></p>`,
+			want: "https://example.com",
+		},
+		{
+			name: "plain text unchanged",
+			html: `<p>No links here.</p>`,
+			want: "No links here.",
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			if got := HTML2TextWithLinks(tt.html); got != tt.want {
+				t.Errorf("got %q, want %q", got, tt.want)
+			}
+		})
+	}
+}