diff --git a/cmd/dev.go b/cmd/dev.go
index bbf4aca8..a197861a 100644
--- a/cmd/dev.go
+++ b/cmd/dev.go
@@ -64,7 +64,7 @@ Examples:
 
 		project, err := theproject.Project.GetProject(ctx, log, theproject.APIURL, apiKey)
 		if err != nil {
-			errsystem.New(errsystem.ErrInvalidConfiguration, err, errsystem.WithContextMessage(fmt.Sprintf("Failed to get project: %s", err))).ShowErrorAndExit()
+			errsystem.New(errsystem.ErrInvalidConfiguration, err, errsystem.WithUserMessage("Failed to validate project (%s) using the provided API key from the .env file in %s. This is most likely due to the API key being invalid or the project has been deleted.", theproject.Project.ProjectId, dir), errsystem.WithContextMessage(fmt.Sprintf("Failed to get project: %s", err))).ShowErrorAndExit()
 		}
 
 		orgId := project.OrgId
diff --git a/internal/errsystem/errsystem.go b/internal/errsystem/errsystem.go
index ca2c97e3..9693d860 100644
--- a/internal/errsystem/errsystem.go
+++ b/internal/errsystem/errsystem.go
@@ -67,9 +67,9 @@ func (e *errSystem) Error() string {
 }
 
 // WithUserMessage adds a user-friendly message to the error.
-func WithUserMessage(message string) option {
+func WithUserMessage(message string, args ...any) option {
 	return func(e *errSystem) {
-		e.message = message
+		e.message = fmt.Sprintf(message, args...)
 	}
 }
 
diff --git a/internal/project/project.go b/internal/project/project.go
index 6fd46d72..45c901e1 100644
--- a/internal/project/project.go
+++ b/internal/project/project.go
@@ -556,7 +556,7 @@ func ResolveProjectDir(logger logger.Logger, cmd *cobra.Command, required bool)
 	cwd, err := os.Getwd()
 	if err != nil {
 		errsystem.New(errsystem.ErrEnvironmentVariablesNotSet, err,
-			errsystem.WithUserMessage(fmt.Sprintf("Failed to get current directory: %s", err))).ShowErrorAndExit()
+			errsystem.WithUserMessage("Failed to get current working directory: %s", err)).ShowErrorAndExit()
 	}
 	dir := cwd
 	dirFlag, _ := cmd.Flags().GetString("dir")
@@ -570,7 +570,7 @@ func ResolveProjectDir(logger logger.Logger, cmd *cobra.Command, required bool)
 	abs, err := filepath.Abs(dir)
 	if err != nil {
 		errsystem.New(errsystem.ErrEnvironmentVariablesNotSet, err,
-			errsystem.WithUserMessage(fmt.Sprintf("Failed to get absolute path: %s", err))).ShowErrorAndExit()
+			errsystem.WithUserMessage("Failed to get absolute path to %s: %s", dir, err)).ShowErrorAndExit()
 	}
 	if !ProjectExists(abs) && required {
 		dir = viper.GetString("preferences.project_dir")