diff --git a/data/generators.go b/data/generators.go
index 7cfe124..99e6eee 100644
--- a/data/generators.go
+++ b/data/generators.go
@@ -342,20 +342,34 @@ func GenerateRandomConversation() model.Conversation {
 	return conversation
 }
 
-func GenerateRandomMessage(participants []string) model.Message {
-	var sender *string = nil
+func randomParticipant(participants []string) *string {
 	if len(participants) == 1 {
 		if rand.Intn(2) == 0 {
-			sender = &participants[0]
+			return &participants[0]
 		}
-	} else {
-		sender = &participants[rand.Intn(len(participants))]
 	}
 
+	return &participants[rand.Intn(len(participants))]
+}
+
+func GenerateRandomMessage(participants []string) model.Message {
+	sender := randomParticipant(participants)
+
 	return model.Message{
 		Text:   GenerateRandomMessageBody(),
-		Guid:   uuid.New().String(),
+		Guid:   uuid.NewString(),
 		Date:   model.Date(time.Now().Add(-1 * time.Duration(rand.Intn(1000000)) * time.Second)),
 		Sender: sender,
 	}
 }
+
+func GenerateAttachmentMessage(participants []string, attachmentGuid string) model.Message {
+	sender := randomParticipant(participants)
+	return model.Message{
+		Text:            "", // todo: try using attachment character here?
+		Guid:            uuid.NewString(),
+		Date:            model.Date(time.Now().Add(-1 * time.Duration(rand.Intn(1000000)) * time.Second)),
+		Sender:          sender,
+		AttachmentGUIDs: []string{attachmentGuid},
+	}
+}
diff --git a/model/message.go b/model/message.go
index d88768a..6f4bb09 100644
--- a/model/message.go
+++ b/model/message.go
@@ -1,8 +1,9 @@
 package model
 
 import (
-	"github.com/rs/zerolog"
 	"time"
+
+	"github.com/rs/zerolog"
 )
 
 type Message struct {
@@ -12,7 +13,8 @@ type Message struct {
 	Date   Date    `json:"date"`
 
 	// Map of attachment GUID to attachment metadata
-	Attachments *map[string]AttributionInfo `json:"attachmentMetadata,omitempty"` // Optional
+	AttachmentGUIDs    []string                    `json:"fileTransferGUIDs,omitempty"`
+	AttachmentMetadata *map[string]AttributionInfo `json:"attachmentMetadata,omitempty"` // Optional
 }
 
 type AttributionInfo struct {
diff --git a/prompt/prompt.go b/prompt/prompt.go
index 0e7959f..111c176 100644
--- a/prompt/prompt.go
+++ b/prompt/prompt.go
@@ -20,8 +20,13 @@ type Prompt struct {
 
 func (p *Prompt) conversationForGUID(guid string) (*model.Conversation, error) {
 	if guid == "*" {
-		// This means any conversation: return the first one
-		return &p.server.SortedConversations()[0], nil
+		// This means any conversation: return the first one (that's not the special Attachments convo)
+		convo := p.server.SortedConversations()[0]
+		if *convo.DisplayName == server.ATTACHMENT_CONVO_DISP_NAME {
+			return &p.server.SortedConversations()[1], nil
+		}
+
+		return &convo, nil
 	}
 
 	return p.server.ConversationForGUID(guid)
@@ -196,7 +201,9 @@ func (p *Prompt) StartInteractive() error {
 			return nil
 
 		default:
-			fmt.Printf("Unknown command: %s\n", line)
+			if len(line) > 0 {
+				fmt.Printf("Unknown command: %s\n", line)
+			}
 		}
 	}
 
diff --git a/resources/resources.go b/resources/resources.go
new file mode 100644
index 0000000..b38ce15
--- /dev/null
+++ b/resources/resources.go
@@ -0,0 +1,6 @@
+package resources
+
+import _ "embed"
+
+//go:embed sedona.jpg
+var TestAttachmentData []byte
diff --git a/resources/sedona.jpg b/resources/sedona.jpg
new file mode 100644
index 0000000..a57f9b0
Binary files /dev/null and b/resources/sedona.jpg differ
diff --git a/server/server.go b/server/server.go
index 5f4cfd1..0bd1a0b 100644
--- a/server/server.go
+++ b/server/server.go
@@ -1,17 +1,24 @@
 package server
 
 import (
+	"bytes"
+	_ "embed"
 	"io"
 	"os"
 	"path"
 	"sort"
+	"time"
 
 	"code.severnaya.net/kordophone-mock/v2/data"
 	"code.severnaya.net/kordophone-mock/v2/model"
+	"code.severnaya.net/kordophone-mock/v2/resources"
+	"github.com/google/uuid"
 	"github.com/rs/zerolog/log"
 )
 
-const VERSION = "KordophoneMock-2.6"
+const VERSION string = "KordophoneMock-2.6"
+
+var ATTACHMENT_CONVO_DISP_NAME string = "Attachments"
 
 const (
 	AUTH_USERNAME = "test"
@@ -129,6 +136,26 @@ func (s *Server) PopulateWithTestData() {
 		convo.LastMessagePreview = lastMessage.Text
 	}
 
+	// Also add an "attachment" conversation
+	attachmentConversation := model.Conversation{
+		Participants: []string{"Attachments"},
+		DisplayName:  &ATTACHMENT_CONVO_DISP_NAME,
+		UnreadCount:  0,
+		Guid:         uuid.New().String(),
+		Date:         model.Date(time.Now()),
+	}
+
+	cs = append(cs, attachmentConversation)
+
+	reader := bytes.NewReader(resources.TestAttachmentData)
+	attachmentGUID, err := s.attachmentStore.StoreAttachment("test.jpg", reader)
+	if err != nil {
+		log.Fatal().Msgf("Error storing test attachment: %s", err)
+	} else {
+		attachmentMessage := data.GenerateAttachmentMessage(attachmentConversation.Participants, *attachmentGUID)
+		s.AppendMessageToConversation(&attachmentConversation, attachmentMessage)
+	}
+
 	s.conversations = cs
 }
 
diff --git a/web/server_test.go b/web/server_test.go
index ca8d443..70c368b 100644
--- a/web/server_test.go
+++ b/web/server_test.go
@@ -312,7 +312,7 @@ func (e MessageUpdateError) Error() string {
 }
 
 func TestUpdatesWebsocket(t *testing.T) {
-	s := web.NewMockHTTPServer(web.MockHTTPServerConfiguration{AuthEnabled: true})
+	s := web.NewMockHTTPServer(web.MockHTTPServerConfiguration{AuthEnabled: false})
 	httpServer := httptest.NewServer(s)
 
 	// Mock conversation