diff --git a/pkg/tools/mcp/mcp.go b/pkg/tools/mcp/mcp.go
index c6fd24ac6..48cf1f956 100644
--- a/pkg/tools/mcp/mcp.go
+++ b/pkg/tools/mcp/mcp.go
@@ -10,6 +10,7 @@ import (
 	"io"
 	"iter"
 	"log/slog"
+	"net"
 	"net/url"
 	"strings"
 	"sync"
@@ -454,12 +455,13 @@ func (ts *Toolset) callTool(ctx context.Context, toolCall tools.ToolCall) (*tool
 
 	resp, err := ts.mcpClient.CallTool(ctx, request)
 
-	// If the server lost our session (e.g. it restarted), force a
-	// reconnection and retry the call once.
-	if errors.Is(err, mcp.ErrSessionMissing) {
-		slog.Warn("MCP session missing, forcing reconnect and retrying", "tool", toolCall.Function.Name, "server", ts.logID)
+	// If the call failed with a connection or session error (e.g. the
+	// server restarted), trigger or wait for a reconnection and retry
+	// the call once.
+	if err != nil && isConnectionError(err) && ctx.Err() == nil {
+		slog.Warn("MCP call failed, forcing reconnect and retrying", "tool", toolCall.Function.Name, "server", ts.logID, "error", err)
 		if waitErr := ts.forceReconnectAndWait(ctx); waitErr != nil {
-			return nil, fmt.Errorf("failed to reconnect after session loss: %w", waitErr)
+			return nil, fmt.Errorf("failed to reconnect after call failure: %w", waitErr)
 		}
 		resp, err = ts.mcpClient.CallTool(ctx, request)
 	}
@@ -690,3 +692,27 @@ func (ts *Toolset) GetPrompt(ctx context.Context, name string, arguments map[str
 	slog.Debug("Retrieved MCP prompt", "prompt", name, "messages_count", len(result.Messages))
 	return result, nil
 }
+
+// isConnectionError reports whether err is a connection or session error
+// that warrants a reconnect-and-retry (as opposed to an application-level
+// error that would fail again even after reconnecting).
+func isConnectionError(err error) bool {
+	if errors.Is(err, mcp.ErrSessionMissing) || errors.Is(err, io.EOF) {
+		return true
+	}
+	var netErr net.Error
+	if errors.As(err, &netErr) {
+		return true
+	}
+	// The MCP SDK wraps transport failures (e.g. connection reset, EOF from
+	// client.Do) with its internal ErrRejected sentinel using %v, which
+	// drops the original error from the chain.  Detect these by checking
+	// the error message for common transport-failure substrings.
+	if msg := err.Error(); strings.Contains(msg, "connection reset") ||
+		strings.Contains(msg, "connection refused") ||
+		strings.Contains(msg, "broken pipe") ||
+		strings.Contains(msg, "EOF") {
+		return true
+	}
+	return false
+}