diff --git a/pkg/app/app.go b/pkg/app/app.go
index eaab62b7..e7356abb 100644
--- a/pkg/app/app.go
+++ b/pkg/app/app.go
@@ -146,8 +146,9 @@ func (a *App) DeprecatedSyncCharts(c DeprecatedChartsConfigProvider) error {
 			SkipRepos:   true,
 			SkipDeps:    true,
 			Concurrency: 2,
-		}, func() {
+		}, func() []error {
 			errs = run.DeprecatedSyncCharts(c)
+			return errs
 		})
 
 		if err != nil {
@@ -181,8 +182,9 @@ func (a *App) Diff(c DiffConfigProvider) error {
 			Validate:               c.Validate(),
 			Concurrency:            c.Concurrency(),
 			IncludeTransitiveNeeds: c.IncludeNeeds(),
-		}, func() {
+		}, func() []error {
 			msg, matched, affected, errs = a.diff(run, c)
+			return errs
 		})
 
 		if msg != nil {
@@ -249,8 +251,9 @@ func (a *App) Template(c TemplateConfigProvider) error {
 			IncludeTransitiveNeeds: c.IncludeNeeds(),
 			Set:                    c.Set(),
 			KubeVersion:            c.KubeVersion(),
-		}, func() {
+		}, func() []error {
 			ok, errs = a.template(run, c)
+			return errs
 		})
 
 		if prepErr != nil {
@@ -268,8 +271,9 @@ func (a *App) WriteValues(c WriteValuesConfigProvider) error {
 			SkipDeps:    c.SkipDeps(),
 			SkipCleanup: c.SkipCleanup(),
 			Concurrency: c.Concurrency(),
-		}, func() {
+		}, func() []error {
 			ok, errs = a.writeValues(run, c)
+			return errs
 		})
 
 		if prepErr != nil {
@@ -320,8 +324,9 @@ func (a *App) Lint(c LintConfigProvider) error {
 			SkipCleanup:            c.SkipCleanup(),
 			Concurrency:            c.Concurrency(),
 			IncludeTransitiveNeeds: c.IncludeNeeds(),
-		}, func() {
+		}, func() []error {
 			ok, lintErrs, errs = a.lint(run, c)
+			return errs
 		})
 
 		if prepErr != nil {
@@ -355,7 +360,8 @@ func (a *App) Fetch(c FetchConfigProvider) error {
 			OutputDir:         c.OutputDir(),
 			OutputDirTemplate: c.OutputDirTemplate(),
 			Concurrency:       c.Concurrency(),
-		}, func() {
+		}, func() []error {
+			return nil
 		})
 
 		if prepErr != nil {
@@ -379,8 +385,9 @@ func (a *App) Sync(c SyncConfigProvider) error {
 			IncludeTransitiveNeeds: c.IncludeNeeds(),
 			Validate:               c.Validate(),
 			Concurrency:            c.Concurrency(),
-		}, func() {
+		}, func() []error {
 			ok, errs = a.sync(run, c)
+			return errs
 		})
 
 		if prepErr != nil {
@@ -413,7 +420,7 @@ func (a *App) Apply(c ApplyConfigProvider) error {
 			Validate:               c.Validate(),
 			Concurrency:            c.Concurrency(),
 			IncludeTransitiveNeeds: c.IncludeNeeds(),
-		}, func() {
+		}, func() []error {
 			matched, updated, es := a.apply(run, c)
 
 			mut.Lock()
@@ -421,6 +428,7 @@ func (a *App) Apply(c ApplyConfigProvider) error {
 			mut.Unlock()
 
 			ok, errs = matched, es
+			return errs
 		})
 
 		if prepErr != nil {
@@ -449,8 +457,9 @@ func (a *App) Status(c StatusesConfigProvider) error {
 			SkipRepos:   true,
 			SkipDeps:    true,
 			Concurrency: c.Concurrency(),
-		}, func() {
+		}, func() []error {
 			ok, errs = a.status(run, c)
+			return errs
 		})
 
 		if err != nil {
@@ -471,8 +480,9 @@ func (a *App) Delete(c DeleteConfigProvider) error {
 				Concurrency:   c.Concurrency(),
 				DeleteWait:    c.DeleteWait(),
 				DeleteTimeout: c.DeleteTimeout(),
-			}, func() {
+			}, func() []error {
 				ok, errs = a.delete(run, c.Purge(), c)
+				return errs
 			})
 
 			if err != nil {
@@ -494,8 +504,9 @@ func (a *App) Destroy(c DestroyConfigProvider) error {
 				Concurrency:   c.Concurrency(),
 				DeleteWait:    c.DeleteWait(),
 				DeleteTimeout: c.DeleteTimeout(),
-			}, func() {
+			}, func() []error {
 				ok, errs = a.delete(run, true, c)
+				return errs
 			})
 			if err != nil {
 				errs = append(errs, err)
@@ -519,8 +530,9 @@ func (a *App) Test(c TestConfigProvider) error {
 			SkipRepos:   c.SkipDeps(),
 			SkipDeps:    c.SkipDeps(),
 			Concurrency: c.Concurrency(),
-		}, func() {
+		}, func() []error {
 			errs = a.test(run, c)
+			return errs
 		})
 
 		if err != nil {
@@ -538,11 +550,12 @@ func (a *App) PrintDAGState(c DAGConfigProvider) error {
 			SkipRepos:   true,
 			SkipDeps:    true,
 			Concurrency: 2,
-		}, func() {
+		}, func() []error {
 			err = a.dag(run)
 			if err != nil {
 				errs = append(errs, err)
 			}
+			return errs
 		})
 		return ok, errs
 	}, false, SetFilter(true))
@@ -554,7 +567,7 @@ func (a *App) PrintState(c StateConfigProvider) error {
 			SkipRepos:   true,
 			SkipDeps:    true,
 			Concurrency: 2,
-		}, func() {
+		}, func() []error {
 			if c.EmbedValues() {
 				for i := range run.state.Releases {
 					r := run.state.Releases[i]
@@ -562,7 +575,7 @@ func (a *App) PrintState(c StateConfigProvider) error {
 					values, err := run.state.LoadYAMLForEmbedding(&r, r.Values, r.MissingFileHandler, r.ValuesPathPrefix)
 					if err != nil {
 						errs = []error{err}
-						return
+						return errs
 					}
 
 					run.state.Releases[i].Values = values
@@ -570,7 +583,7 @@ func (a *App) PrintState(c StateConfigProvider) error {
 					secrets, err := run.state.LoadYAMLForEmbedding(&r, r.Secrets, r.MissingFileHandler, r.ValuesPathPrefix)
 					if err != nil {
 						errs = []error{err}
-						return
+						return errs
 					}
 
 					run.state.Releases[i].Secrets = secrets
@@ -580,17 +593,18 @@ func (a *App) PrintState(c StateConfigProvider) error {
 			stateYaml, err := run.state.ToYaml()
 			if err != nil {
 				errs = []error{err}
-				return
+				return errs
 			}
 
 			sourceFile, err := run.state.FullFilePath()
 			if err != nil {
 				errs = []error{err}
-				return
+				return errs
 			}
 			fmt.Printf("---\n#  Source: %s\n\n%+v", sourceFile, stateYaml)
 
 			errs = []error{}
+			return errs
 		})
 
 		if err != nil {
@@ -626,12 +640,13 @@ func (a *App) ListReleases(c ListConfigProvider) error {
 				SkipRepos:   true,
 				SkipDeps:    true,
 				Concurrency: 2,
-			}, func() {
+			}, func() []error {
 				rel, err := a.list(run)
 				if err != nil {
 					panic(err)
 				}
 				stateReleases = rel
+				return nil
 			})
 		} else {
 			stateReleases, err = a.list(run)
diff --git a/pkg/app/run.go b/pkg/app/run.go
index e29fce2a..a9d77e08 100644
--- a/pkg/app/run.go
+++ b/pkg/app/run.go
@@ -55,7 +55,7 @@ func (r *Run) prepareChartsIfNeeded(helmfileCommand string, dir string, concurre
 	return releaseToChart, nil
 }
 
-func (r *Run) withPreparedCharts(helmfileCommand string, opts state.ChartPrepareOptions, f func()) error {
+func (r *Run) withPreparedCharts(helmfileCommand string, opts state.ChartPrepareOptions, f func() []error) error {
 	if r.ReleaseToChart != nil {
 		panic("Run.PrepareCharts can be called only once")
 	}
@@ -111,9 +111,13 @@ func (r *Run) withPreparedCharts(helmfileCommand string, opts state.ChartPrepare
 
 	r.ReleaseToChart = releaseToChart
 
-	f()
+	errs := f()
+	var firstErr error = nil
+	if len(errs) > 0 {
+		firstErr = errs[0]
+	}
 
-	_, err = r.state.TriggerGlobalCleanupEvent(helmfileCommand)
+	_, err = r.state.TriggerGlobalCleanupEvent(helmfileCommand, firstErr)
 	return err
 }
 
diff --git a/pkg/state/state.go b/pkg/state/state.go
index 0fbff129..32e6fc9e 100644
--- a/pkg/state/state.go
+++ b/pkg/state/state.go
@@ -2400,8 +2400,8 @@ func (st *HelmState) TriggerGlobalPrepareEvent(helmfileCommand string) (bool, er
 	return st.triggerGlobalReleaseEvent("prepare", nil, helmfileCommand)
 }
 
-func (st *HelmState) TriggerGlobalCleanupEvent(helmfileCommand string) (bool, error) {
-	return st.triggerGlobalReleaseEvent("cleanup", nil, helmfileCommand)
+func (st *HelmState) TriggerGlobalCleanupEvent(helmfileCommand string, evtErr error) (bool, error) {
+	return st.triggerGlobalReleaseEvent("cleanup", evtErr, helmfileCommand)
 }
 
 func (st *HelmState) triggerGlobalReleaseEvent(evt string, evtErr error, helmfileCmd string) (bool, error) {