diff --git a/go.mod b/go.mod
index ebc590da..2de281cf 100644
--- a/go.mod
+++ b/go.mod
@@ -3,6 +3,7 @@ module github.com/helmfile/helmfile
 go 1.25.4
 
 require (
+	al.essio.dev/pkg/shellescape v1.6.0
 	dario.cat/mergo v1.0.2
 	github.com/Masterminds/semver/v3 v3.4.0
 	github.com/Masterminds/sprig/v3 v3.3.0
@@ -110,7 +111,6 @@ require (
 )
 
 require (
-	al.essio.dev/pkg/shellescape v1.6.0 // indirect
 	cel.dev/expr v0.24.0 // indirect
 	cloud.google.com/go/auth v0.17.0 // indirect
 	cloud.google.com/go/auth/oauth2adapt v0.2.8 // indirect
diff --git a/pkg/state/state.go b/pkg/state/state.go
index f3cb0887..38b92b22 100644
--- a/pkg/state/state.go
+++ b/pkg/state/state.go
@@ -1441,18 +1441,26 @@ func (st *HelmState) processChartification(chartification *Chartify, release *Re
 				chartifyOpts.TemplateArgs = fmt.Sprintf("--kube-context %s --dry-run=server", quotedContext)
 			} else {
 				// Only add --kube-context if not already present
-				if !strings.Contains(chartifyOpts.TemplateArgs, "--kube-context") {
+				// Check for the flag at word boundaries to avoid false matches
+				if !strings.Contains(chartifyOpts.TemplateArgs, "--kube-context ") &&
+					!strings.HasPrefix(chartifyOpts.TemplateArgs, "--kube-context=") &&
+					!strings.Contains(chartifyOpts.TemplateArgs, " --kube-context=") {
 					chartifyOpts.TemplateArgs = fmt.Sprintf("--kube-context %s %s", quotedContext, chartifyOpts.TemplateArgs)
 				}
 				// Add --dry-run if not already present
-				if !strings.Contains(chartifyOpts.TemplateArgs, "--dry-run") {
+				// Check for the flag at word boundaries to avoid false matches
+				if !strings.Contains(chartifyOpts.TemplateArgs, "--dry-run ") &&
+					!strings.HasPrefix(chartifyOpts.TemplateArgs, "--dry-run=") &&
+					!strings.Contains(chartifyOpts.TemplateArgs, " --dry-run=") {
 					chartifyOpts.TemplateArgs += " --dry-run=server"
 				}
 			}
 		} else {
 			if chartifyOpts.TemplateArgs == "" {
 				chartifyOpts.TemplateArgs = "--dry-run=server"
-			} else if !strings.Contains(chartifyOpts.TemplateArgs, "--dry-run") {
+			} else if !strings.Contains(chartifyOpts.TemplateArgs, "--dry-run ") &&
+				!strings.HasPrefix(chartifyOpts.TemplateArgs, "--dry-run=") &&
+				!strings.Contains(chartifyOpts.TemplateArgs, " --dry-run=") {
 				chartifyOpts.TemplateArgs += " --dry-run=server"
 			}
 		}