diff --git a/go.mod b/go.mod
index 8493b6b..2db2da3 100644
--- a/go.mod
+++ b/go.mod
@@ -5,13 +5,13 @@ go 1.23.0
 require (
 	github.com/anthropics/anthropic-sdk-go v1.22.0
 	github.com/mattn/go-sqlite3 v1.14.33
+	github.com/robfig/cron/v3 v3.0.1
 	github.com/slack-go/slack v0.17.3
 	gopkg.in/yaml.v3 v3.0.1
 )
 
 require (
 	github.com/gorilla/websocket v1.5.3 // indirect
-	github.com/robfig/cron/v3 v3.0.1 // indirect
 	github.com/tidwall/gjson v1.18.0 // indirect
 	github.com/tidwall/match v1.1.1 // indirect
 	github.com/tidwall/pretty v1.2.1 // indirect
diff --git a/slack.go b/slack.go
index b0a043c..826a809 100644
--- a/slack.go
+++ b/slack.go
@@ -363,7 +363,17 @@ func handleGenerateReport(api *slack.Client, db *sql.DB, cfg Config, cmd slack.S
 	if mode == "boss" {
 		teamReportFile := fmt.Sprintf("%s_%s.md", cfg.TeamName, friday.Format("20060102"))
 		teamReportPath := filepath.Join(cfg.ReportOutputDir, teamReportFile)
-		if content, readErr := os.ReadFile(teamReportPath); readErr == nil && len(content) > 0 {
+		content, readErr := os.ReadFile(teamReportPath)
+		if readErr != nil {
+			if !os.IsNotExist(readErr) {
+				// Unexpected error (permission, I/O, etc.) - surface it and abort
+				log.Printf("Error reading team report file %s: %v", teamReportPath, readErr)
+				postEphemeral(api, cmd, fmt.Sprintf("Error reading team report file: %v", readErr))
+				return
+			}
+			// File doesn't exist - fall through to full pipeline below
+			log.Printf("generate-report boss: no existing team report found, running full pipeline")
+		} else if len(content) > 0 {
 			log.Printf("generate-report boss: deriving from existing team report %s", teamReportPath)
 			template := parseTemplate(string(content))
 			stripCurrentTeamTitleFromPrefix(template, cfg.TeamName)
@@ -414,7 +424,6 @@ func handleGenerateReport(api *slack.Client, db *sql.DB, cfg Config, cmd slack.S
 			log.Printf("generate-report done mode=boss derived-from-team")
 			return
 		}
-		log.Printf("generate-report boss: no existing team report found, running full pipeline")
 	}
 
 	items, err := GetItemsByDateRange(db, monday, nextMonday)