diff --git a/internal/llm/agent/agent.go b/internal/llm/agent/agent.go
index fbb5b4fd8c6390ff0dfad0e072af35342355ba41..3d2012f04812c234bd9f50cb7c2246c977c190de 100644
--- a/internal/llm/agent/agent.go
+++ b/internal/llm/agent/agent.go
@@ -403,7 +403,7 @@ func (a *agent) processGeneration(ctx context.Context, sessionID, content string
 		agentMessage, toolResults, err := a.streamAndHandleEvents(ctx, sessionID, msgHistory)
 		if err != nil {
 			if errors.Is(err, context.Canceled) {
-				agentMessage.AddFinish(message.FinishReasonCanceled)
+				agentMessage.AddFinish(message.FinishReasonCanceled, "Request cancelled", "")
 				a.messages.Update(context.Background(), agentMessage)
 				return a.err(ErrRequestCancelled)
 			}
@@ -454,11 +454,15 @@ func (a *agent) streamAndHandleEvents(ctx context.Context, sessionID string, msg
 	// Process each event in the stream.
 	for event := range eventChan {
 		if processErr := a.processEvent(ctx, sessionID, &assistantMsg, event); processErr != nil {
-			a.finishMessage(ctx, &assistantMsg, message.FinishReasonCanceled)
+			if errors.Is(processErr, context.Canceled) {
+				a.finishMessage(context.Background(), &assistantMsg, message.FinishReasonCanceled, "Request cancelled", "")
+			} else {
+				a.finishMessage(ctx, &assistantMsg, message.FinishReasonError, "API Error", processErr.Error())
+			}
 			return assistantMsg, nil, processErr
 		}
 		if ctx.Err() != nil {
-			a.finishMessage(context.Background(), &assistantMsg, message.FinishReasonCanceled)
+			a.finishMessage(context.Background(), &assistantMsg, message.FinishReasonCanceled, "Request cancelled", "")
 			return assistantMsg, nil, ctx.Err()
 		}
 	}
@@ -468,7 +472,7 @@ func (a *agent) streamAndHandleEvents(ctx context.Context, sessionID string, msg
 	for i, toolCall := range toolCalls {
 		select {
 		case <-ctx.Done():
-			a.finishMessage(context.Background(), &assistantMsg, message.FinishReasonCanceled)
+			a.finishMessage(context.Background(), &assistantMsg, message.FinishReasonCanceled, "Request cancelled", "")
 			// Make all future tool calls cancelled
 			for j := i; j < len(toolCalls); j++ {
 				toolResults[j] = message.ToolResult{
@@ -516,7 +520,7 @@ func (a *agent) streamAndHandleEvents(ctx context.Context, sessionID string, msg
 							IsError:    true,
 						}
 					}
-					a.finishMessage(ctx, &assistantMsg, message.FinishReasonPermissionDenied)
+					a.finishMessage(ctx, &assistantMsg, message.FinishReasonPermissionDenied, "Permission denied", "")
 					break
 				}
 			}
@@ -548,8 +552,8 @@ out:
 	return assistantMsg, &msg, err
 }
 
-func (a *agent) finishMessage(ctx context.Context, msg *message.Message, finishReson message.FinishReason) {
-	msg.AddFinish(finishReson)
+func (a *agent) finishMessage(ctx context.Context, msg *message.Message, finishReson message.FinishReason, message, details string) {
+	msg.AddFinish(finishReson, message, details)
 	_ = a.messages.Update(ctx, *msg)
 }
 
@@ -580,15 +584,10 @@ func (a *agent) processEvent(ctx context.Context, sessionID string, assistantMsg
 		assistantMsg.FinishToolCall(event.ToolCall.ID)
 		return a.messages.Update(ctx, *assistantMsg)
 	case provider.EventError:
-		if errors.Is(event.Error, context.Canceled) {
-			slog.Info(fmt.Sprintf("Event processing canceled for session: %s", sessionID))
-			return context.Canceled
-		}
-		slog.Error(event.Error.Error())
 		return event.Error
 	case provider.EventComplete:
 		assistantMsg.SetToolCalls(event.Response.ToolCalls)
-		assistantMsg.AddFinish(event.Response.FinishReason)
+		assistantMsg.AddFinish(event.Response.FinishReason, "", "")
 		if err := a.messages.Update(ctx, *assistantMsg); err != nil {
 			return fmt.Errorf("failed to update message: %w", err)
 		}
diff --git a/internal/message/content.go b/internal/message/content.go
index 3ab53e381aaf7755c141985ebe740dbc44356471..b8d2c1aa370559977f4c8eb80803ab5fbfe83cf9 100644
--- a/internal/message/content.go
+++ b/internal/message/content.go
@@ -102,8 +102,10 @@ type ToolResult struct {
 func (ToolResult) isPart() {}
 
 type Finish struct {
-	Reason FinishReason `json:"reason"`
-	Time   int64        `json:"time"`
+	Reason  FinishReason `json:"reason"`
+	Time    int64        `json:"time"`
+	Message string       `json:"message,omitempty"`
+	Details string       `json:"details,omitempty"`
 }
 
 func (Finish) isPart() {}
@@ -308,7 +310,7 @@ func (m *Message) SetToolResults(tr []ToolResult) {
 	}
 }
 
-func (m *Message) AddFinish(reason FinishReason) {
+func (m *Message) AddFinish(reason FinishReason, message, details string) {
 	// remove any existing finish part
 	for i, part := range m.Parts {
 		if _, ok := part.(Finish); ok {
@@ -316,7 +318,7 @@ func (m *Message) AddFinish(reason FinishReason) {
 			break
 		}
 	}
-	m.Parts = append(m.Parts, Finish{Reason: reason, Time: time.Now().Unix()})
+	m.Parts = append(m.Parts, Finish{Reason: reason, Time: time.Now().Unix(), Message: message, Details: details})
 }
 
 func (m *Message) AddImageURL(url, detail string) {
diff --git a/internal/tui/components/chat/messages/messages.go b/internal/tui/components/chat/messages/messages.go
index e8ae97056728a0377ddcad179ecae1246f2da662..657533d9f0f13fcad404f76d8e19999710800050 100644
--- a/internal/tui/components/chat/messages/messages.go
+++ b/internal/tui/components/chat/messages/messages.go
@@ -8,6 +8,7 @@ import (
 
 	tea "github.com/charmbracelet/bubbletea/v2"
 	"github.com/charmbracelet/lipgloss/v2"
+	"github.com/charmbracelet/x/ansi"
 
 	"github.com/charmbracelet/crush/internal/config"
 	"github.com/charmbracelet/crush/internal/fur/provider"
@@ -184,6 +185,7 @@ func (m *messageCmp) toMarkdown(content string) string {
 // markdownContent processes the message content and handles special states.
 // Returns appropriate content for thinking, finished, and error states.
 func (m *messageCmp) markdownContent() string {
+	t := styles.CurrentTheme()
 	content := m.message.Content().String()
 	if m.message.Role == message.Assistant {
 		thinking := m.message.IsThinking()
@@ -199,6 +201,13 @@ func (m *messageCmp) markdownContent() string {
 			content = ""
 		} else if finished && content == "" && finishedData.Reason == message.FinishReasonCanceled {
 			content = "*Canceled*"
+		} else if finished && content == "" && finishedData.Reason == message.FinishReasonError {
+			errTag := t.S().Base.Padding(0, 1).Background(t.Red).Foreground(t.White).Render("ERROR")
+			truncated := ansi.Truncate(finishedData.Message, m.textWidth()-2-lipgloss.Width(errTag), "...")
+			title := fmt.Sprintf("%s %s", errTag, t.S().Base.Foreground(t.FgHalfMuted).Render(truncated))
+			details := t.S().Base.Foreground(t.FgSubtle).Width(m.textWidth() - 2).Render(finishedData.Details)
+			return fmt.Sprintf("%s\n\n%s", title, details)
+
 		}
 	}
 	return m.toMarkdown(content)