diff --git a/devbox.json b/devbox.json
index 48f4240cbb0..0253af59b7f 100644
--- a/devbox.json
+++ b/devbox.json
@@ -5,6 +5,8 @@
     "go":                          "latest",
     "runx:golangci/golangci-lint": "latest",
     "runx:mvdan/gofumpt":          "latest",
+
+    "hello": "latest",
   },
   "env": {
     "GOENV": "off",
diff --git a/devbox.lock b/devbox.lock
index 6237e47e5f3..86908fc1282 100644
--- a/devbox.lock
+++ b/devbox.lock
@@ -49,6 +49,54 @@
         }
       }
     },
+    "hello@latest": {
+      "last_modified": "2024-10-13T23:44:06Z",
+      "resolved": "github:NixOS/nixpkgs/d4f247e89f6e10120f911e2e2d2254a050d0f732#hello",
+      "source": "devbox-search",
+      "version": "2.12.1",
+      "systems": {
+        "aarch64-darwin": {
+          "outputs": [
+            {
+              "name": "out",
+              "path": "/nix/store/8fpvkfwr8fm91xlzznsgh3g1fcw0hfnh-hello-2.12.1",
+              "default": true
+            }
+          ],
+          "store_path": "/nix/store/8fpvkfwr8fm91xlzznsgh3g1fcw0hfnh-hello-2.12.1"
+        },
+        "aarch64-linux": {
+          "outputs": [
+            {
+              "name": "out",
+              "path": "/nix/store/9i2ay9whhyswa2cc30azxiyqrjb795xj-hello-2.12.1",
+              "default": true
+            }
+          ],
+          "store_path": "/nix/store/9i2ay9whhyswa2cc30azxiyqrjb795xj-hello-2.12.1"
+        },
+        "x86_64-darwin": {
+          "outputs": [
+            {
+              "name": "out",
+              "path": "/nix/store/h6lx6hmccksq64nsa4h3c8p9gl1vzqcf-hello-2.12.1",
+              "default": true
+            }
+          ],
+          "store_path": "/nix/store/h6lx6hmccksq64nsa4h3c8p9gl1vzqcf-hello-2.12.1"
+        },
+        "x86_64-linux": {
+          "outputs": [
+            {
+              "name": "out",
+              "path": "/nix/store/26xbg1ndr7hbcncrlf9nhx5is2b25d13-hello-2.12.1",
+              "default": true
+            }
+          ],
+          "store_path": "/nix/store/26xbg1ndr7hbcncrlf9nhx5is2b25d13-hello-2.12.1"
+        }
+      }
+    },
     "runx:golangci/golangci-lint@latest": {
       "resolved": "golangci/golangci-lint@v1.60.2",
       "version": "v1.60.2"
diff --git a/internal/boxcli/run.go b/internal/boxcli/run.go
index 123288b5039..2372142304e 100644
--- a/internal/boxcli/run.go
+++ b/internal/boxcli/run.go
@@ -17,6 +17,7 @@ import (
 	"go.jetpack.io/devbox/internal/devbox"
 	"go.jetpack.io/devbox/internal/devbox/devopt"
 	"go.jetpack.io/devbox/internal/redact"
+	"go.jetpack.io/devbox/internal/ux"
 )
 
 type runCmdFlags struct {
@@ -122,13 +123,22 @@ func runScriptCmd(cmd *cobra.Command, args []string, flags runCmdFlags) error {
 		return redact.Errorf("error reading devbox.json: %w", err)
 	}
 
+	onStaleState := func() {
+		ux.FHidableWarning(
+			ctx,
+			cmd.ErrOrStderr(),
+			devbox.StateOutOfDateMessage,
+			"with --recompute=true",
+		)
+	}
+
 	envOpts := devopt.EnvOptions{
-		OmitNixEnv: flags.omitNixEnv,
-		Pure:       flags.pure,
-		RecomputeEnv: &devopt.RecomputeEnvOpts{
-			Disabled:              !flags.recomputeEnv,
-			StateOutOfDateMessage: fmt.Sprintf(devbox.StateOutOfDateMessage, "with --recompute=true"),
+		Hooks: devopt.EnvLifecycleHooks{
+			OnSkipRecomputeDespiteStaleState: onStaleState,
 		},
+		OmitNixEnv:       flags.omitNixEnv,
+		Pure:             flags.pure,
+		SkipRecomputeEnv: !flags.recomputeEnv,
 	}
 	if err := box.RunScript(ctx, envOpts, script, scriptArgs); err != nil {
 		return redact.Errorf("error running script %q in Devbox: %w", script, err)
diff --git a/internal/boxcli/shell.go b/internal/boxcli/shell.go
index 60575549f9f..91f9ca9a362 100644
--- a/internal/boxcli/shell.go
+++ b/internal/boxcli/shell.go
@@ -13,6 +13,7 @@ import (
 	"go.jetpack.io/devbox/internal/devbox"
 	"go.jetpack.io/devbox/internal/devbox/devopt"
 	"go.jetpack.io/devbox/internal/envir"
+	"go.jetpack.io/devbox/internal/ux"
 )
 
 type shellCmdFlags struct {
@@ -95,13 +96,22 @@ func runShellCmd(cmd *cobra.Command, flags shellCmdFlags) error {
 		return shellInceptionErrorMsg("devbox shell")
 	}
 
+	onStaleState := func() {
+		ux.FHidableWarning(
+			ctx,
+			cmd.ErrOrStderr(),
+			devbox.StateOutOfDateMessage,
+			"with --recompute=true",
+		)
+	}
+
 	return box.Shell(ctx, devopt.EnvOptions{
-		OmitNixEnv: flags.omitNixEnv,
-		Pure:       flags.pure,
-		RecomputeEnv: &devopt.RecomputeEnvOpts{
-			Disabled:              !flags.recomputeEnv,
-			StateOutOfDateMessage: fmt.Sprintf(devbox.StateOutOfDateMessage, "with --recompute=true"),
+		Hooks: devopt.EnvLifecycleHooks{
+			OnSkipRecomputeDespiteStaleState: onStaleState,
 		},
+		OmitNixEnv:       flags.omitNixEnv,
+		Pure:             flags.pure,
+		SkipRecomputeEnv: !flags.recomputeEnv,
 	})
 }
 
diff --git a/internal/boxcli/shellenv.go b/internal/boxcli/shellenv.go
index a783e091306..7742a3fffed 100644
--- a/internal/boxcli/shellenv.go
+++ b/internal/boxcli/shellenv.go
@@ -115,15 +115,24 @@ func shellEnvFunc(
 		}
 	}
 
+	onStaleState := func() {
+		ux.FHidableWarning(
+			ctx,
+			cmd.ErrOrStderr(),
+			devbox.StateOutOfDateMessage,
+			"devbox install",
+		)
+	}
+
 	envStr, err := box.EnvExports(ctx, devopt.EnvExportsOpts{
 		EnvOptions: devopt.EnvOptions{
+			Hooks: devopt.EnvLifecycleHooks{
+				OnSkipRecomputeDespiteStaleState: onStaleState,
+			},
 			OmitNixEnv:        flags.omitNixEnv,
 			PreservePathStack: flags.preservePathStack,
 			Pure:              flags.pure,
-			RecomputeEnv: &devopt.RecomputeEnvOpts{
-				Disabled:              !flags.recomputeEnv,
-				StateOutOfDateMessage: fmt.Sprintf(devbox.StateOutOfDateMessage, box.RefreshAliasOrCommand()),
-			},
+			SkipRecomputeEnv:  !flags.recomputeEnv,
 		},
 		NoRefreshAlias: flags.noRefreshAlias,
 		RunHooks:       flags.runInitHook,
diff --git a/internal/devbox/devbox.go b/internal/devbox/devbox.go
index 2083e363ab0..5919a56f6e8 100644
--- a/internal/devbox/devbox.go
+++ b/internal/devbox/devbox.go
@@ -804,14 +804,12 @@ func (d *Devbox) ensureStateIsUpToDateAndComputeEnv(
 ) (map[string]string, error) {
 	defer debug.FunctionTimer().End()
 
-	if envOpts.RecomputeEnv.Disabled {
+	if envOpts.SkipRecomputeEnv {
 		upToDate, _ := d.lockfile.IsUpToDateAndInstalled(isFishShell())
 		if !upToDate {
-			ux.FHidableWarning(
-				ctx,
-				d.stderr,
-				envOpts.RecomputeEnv.StateOutOfDateMessage, //nolint:govet
-			)
+			if envOpts.Hooks.OnSkipRecomputeDespiteStaleState != nil {
+				envOpts.Hooks.OnSkipRecomputeDespiteStaleState()
+			}
 		}
 	} else {
 		// When ensureStateIsUpToDate is called with ensure=true, it always
diff --git a/internal/devbox/devopt/devboxopts.go b/internal/devbox/devopt/devboxopts.go
index 4ee64f9dd40..e7e7871b43e 100644
--- a/internal/devbox/devopt/devboxopts.go
+++ b/internal/devbox/devopt/devboxopts.go
@@ -72,13 +72,14 @@ type EnvExportsOpts struct {
 // like `shellenv`, `shell` and `run`.
 // - The struct is designed for the "common case" to be zero-initialized as `EnvOptions{}`.
 type EnvOptions struct {
+	Hooks             EnvLifecycleHooks
 	OmitNixEnv        bool
 	PreservePathStack bool
 	Pure              bool
-	RecomputeEnv      *RecomputeEnvOpts
+	SkipRecomputeEnv  bool
 }
 
-type RecomputeEnvOpts struct {
-	Disabled              bool // Disabled instead of Enabled, because zero-value is false
-	StateOutOfDateMessage string
+type EnvLifecycleHooks struct {
+	// OnSkipRecomputeDespiteStaleState is called when the Devbox state is out of date, AND it is not being recomputed.
+	OnSkipRecomputeDespiteStaleState func()
 }