diff --git a/cmd/cloud.go b/cmd/cloud.go
index a6e21d1a..0f83ce8a 100644
--- a/cmd/cloud.go
+++ b/cmd/cloud.go
@@ -25,6 +25,7 @@ import (
 	"github.com/agentuity/go-common/logger"
 	cstr "github.com/agentuity/go-common/string"
 	"github.com/agentuity/go-common/tui"
+	"github.com/charmbracelet/lipgloss"
 	"github.com/spf13/cobra"
 	"github.com/spf13/viper"
 	"k8s.io/apimachinery/pkg/api/resource"
@@ -121,6 +122,63 @@ func ShowNewProjectImport(ctx context.Context, logger logger.Logger, cmd *cobra.
 	tui.ShowSuccess("Project imported successfully")
 }
 
+var envTemplateFileNames = []string{".env.example", ".env.template"}
+
+func readPossibleEnvTemplateFiles(baseDir string) map[string][]env.EnvLineComment {
+	var results map[string][]env.EnvLineComment
+	keys := make(map[string]bool)
+	for _, file := range envTemplateFileNames {
+		filename := filepath.Join(baseDir, file)
+		if !util.Exists(filename) {
+			continue
+		}
+		efc, err := env.ParseEnvFileWithComments(filename)
+		if err == nil {
+			if results == nil {
+				results = make(map[string][]env.EnvLineComment)
+			}
+			for _, ev := range efc {
+				if _, ok := keys[ev.Key]; !ok {
+					if isAgentuityEnv.MatchString(ev.Key) {
+						continue
+					}
+					keys[ev.Key] = true
+					results[file] = append(results[file], ev)
+				}
+			}
+		}
+	}
+	return results
+}
+
+func appendToEnvFile(envfile string, envs []env.EnvLineComment) ([]env.EnvLineComment, error) {
+	le, err := env.ParseEnvFileWithComments(envfile)
+	if err != nil {
+		return nil, err
+	}
+	var buf strings.Builder
+	for _, ev := range le {
+		if ev.Comment != "" {
+			buf.WriteString(fmt.Sprintf("# %s\n", ev.Comment))
+		}
+		buf.WriteString(fmt.Sprintf("%s=%s\n", ev.Key, ev.Raw))
+	}
+	for _, ev := range envs {
+		if ev.Comment != "" {
+			buf.WriteString(fmt.Sprintf("# %s\n", ev.Comment))
+		}
+		buf.WriteString(fmt.Sprintf("%s=%s\n", ev.Key, ev.Raw))
+		le = append(le, ev)
+	}
+	if err := os.WriteFile(envfile, []byte(buf.String()), 0644); err != nil {
+		return nil, err
+	}
+	return le, nil
+}
+
+var border = lipgloss.NewStyle().Border(lipgloss.NormalBorder()).Padding(1).BorderForeground(lipgloss.AdaptiveColor{Light: "#999999", Dark: "#999999"})
+var redDiff = lipgloss.NewStyle().Foreground(lipgloss.AdaptiveColor{Light: "#990000", Dark: "#EE0000"})
+
 var cloudDeployCmd = &cobra.Command{
 	Use:   "deploy",
 	Short: "Deploy project to the cloud",
@@ -193,7 +251,7 @@ Examples:
 			}
 
 			var err error
-			var le []env.EnvLine
+			var le []env.EnvLineComment
 			var projectExists bool
 			var action func()
 
@@ -228,13 +286,80 @@ Examples:
 			envfilename := filepath.Join(dir, ".env")
 			if tui.HasTTY && util.Exists(envfilename) {
 
-				le, err = env.ParseEnvFile(envfilename)
+				// attempt to see if we have any template files
+				templateEnvs := readPossibleEnvTemplateFiles(dir)
+
+				le, err = env.ParseEnvFileWithComments(envfilename)
 				if err != nil {
 					errsystem.New(errsystem.ErrParseEnvironmentFile, err,
 						errsystem.WithContextMessage("Error parsing .env file")).ShowErrorAndExit()
 				}
 				envFile = &deployer.EnvFile{Filepath: envfilename, Env: le}
 
+				if len(templateEnvs) > 0 {
+					kvmap := make(map[string]env.EnvLineComment)
+					for _, ev := range le {
+						if isAgentuityEnv.MatchString(ev.Key) {
+							continue
+						}
+						kvmap[ev.Key] = ev
+					}
+					var osenv map[string]string
+					var addtoenvfile []env.EnvLineComment
+					// look to see if we have any template environment variables that are not in the .env file
+					for filename, evs := range templateEnvs {
+						for _, ev := range evs {
+							if _, ok := kvmap[ev.Key]; !ok {
+								isSecret := looksLikeSecret.MatchString(ev.Key)
+								if !isSecret && descriptionLookingLikeASecret(ev.Comment) {
+									isSecret = true
+								}
+								_ = filename
+								var content string
+								var para []string
+								para = append(para, tui.Warning("Missing Environment Variable\n"))
+								para = append(para, fmt.Sprintf("The variable %s was found in %s but not in your %s file:\n", tui.Bold(ev.Key), tui.Bold(filename), tui.Bold(".env")))
+								if ev.Comment != "" {
+									para = append(para, tui.Muted(fmt.Sprintf("# %s", ev.Comment)))
+								}
+								if isSecret {
+									para = append(para, redDiff.Render(fmt.Sprintf("+ %s=%s\n", ev.Key, cstr.Mask(ev.Val))))
+								} else {
+									para = append(para, redDiff.Render(fmt.Sprintf("+ %s=%s\n", ev.Key, ev.Val)))
+								}
+								content = lipgloss.JoinVertical(lipgloss.Left, para...)
+								fmt.Println(border.Render(content))
+								if !tui.Ask(logger, "Would you like to add it to your .env file?", true) {
+									fmt.Println()
+									tui.ShowWarning("cancelled")
+									continue
+								}
+								if osenv == nil {
+									osenv = loadOSEnv()
+								}
+								val := promptForEnv(logger, ev.Key, isSecret, nil, osenv, ev.Val, ev.Comment)
+								addtoenvfile = append(addtoenvfile, env.EnvLineComment{
+									EnvLine: env.EnvLine{
+										Key: ev.Key,
+										Val: val,
+										Raw: val,
+									},
+									Comment: ev.Comment,
+								})
+							}
+						}
+					}
+					if len(addtoenvfile) > 0 {
+						le, err = appendToEnvFile(envfilename, addtoenvfile)
+						if err != nil {
+							errsystem.New(errsystem.ErrParseEnvironmentFile, err,
+								errsystem.WithContextMessage("Error parsing .env file")).ShowErrorAndExit()
+						}
+						tui.ShowSuccess("added %s to your .env file", util.Pluralize(len(addtoenvfile), "environment variable", "environment variables"))
+						fmt.Println()
+					}
+				}
+
 				var foundkeys []string
 				for _, ev := range le {
 					if isAgentuityEnv.MatchString(ev.Key) {
@@ -250,15 +375,25 @@ Examples:
 				}
 				if len(foundkeys) > 0 {
 					var title string
+					var suffix string
 					switch {
 					case len(foundkeys) < 3 && len(foundkeys) > 1:
-						title = fmt.Sprintf("The environment variables %s from .env are not been set in the project. Would you like to add it?", strings.Join(foundkeys, ", "))
+						suffix = "it"
+						var colorized []string
+						for _, key := range foundkeys {
+							colorized = append(colorized, tui.Bold(key))
+						}
+						title = fmt.Sprintf("The environment variables %s from %s are not been set in the project.", strings.Join(colorized, ", "), tui.Bold(".env"))
 					case len(foundkeys) == 1:
-						title = fmt.Sprintf("The environment variable %s from .env has not been set in the project. Would you like to add it?", foundkeys[0])
+						suffix = "it"
+						title = fmt.Sprintf("The environment variable %s from %s has not been set in the project.", tui.Bold(foundkeys[0]), tui.Bold(".env"))
 					default:
-						title = fmt.Sprintf("There are %d environment variables from .env that are not set in the project. Would you like to add them?", len(foundkeys))
+						suffix = "them"
+						title = fmt.Sprintf("There are %d environment variables from %s that are not set in the project.", len(foundkeys), tui.Bold(".env"))
 					}
-					if !tui.Ask(logger, title, true) {
+					fmt.Println(title)
+					if !tui.Ask(logger, "Would you like to set "+suffix+"?", true) {
+						fmt.Println()
 						tui.ShowWarning("cancelled")
 						return
 					}
@@ -271,6 +406,8 @@ Examples:
 						errsystem.New(errsystem.ErrEnvironmentVariablesNotSet, err,
 							errsystem.WithContextMessage("Failed to set project environment variables")).ShowErrorAndExit()
 					}
+					fmt.Println()
+					fmt.Println()
 					projectData = pd // overwrite with the new version
 					switch {
 					case len(envs) > 0 && len(secrets) > 0:
@@ -284,6 +421,7 @@ Examples:
 					case len(secrets) > 1:
 						tui.ShowSuccess("Secrets added")
 					}
+					fmt.Println()
 				}
 			}
 
diff --git a/cmd/dev.go b/cmd/dev.go
index 220766ba..430c74fb 100644
--- a/cmd/dev.go
+++ b/cmd/dev.go
@@ -6,7 +6,6 @@ import (
 	"io"
 	"os"
 	"os/signal"
-	"runtime"
 	"strings"
 	"syscall"
 	"time"
@@ -44,12 +43,7 @@ Examples:
 		logLevel := env.LogLevel(cmd)
 		apiUrl, appUrl, transportUrl := util.GetURLs(log)
 
-		signals := []os.Signal{os.Interrupt, syscall.SIGINT}
-		if runtime.GOOS != "windows" {
-			signals = append(signals, syscall.SIGTERM)
-		}
-
-		ctx, cancel := signal.NotifyContext(context.Background(), signals...)
+		ctx, cancel := signal.NotifyContext(context.Background(), os.Interrupt, syscall.SIGINT, syscall.SIGTERM)
 		defer cancel()
 
 		apiKey, userId := util.EnsureLoggedIn(ctx, log, cmd)
diff --git a/cmd/env.go b/cmd/env.go
index e6ee3698..a0077ab1 100644
--- a/cmd/env.go
+++ b/cmd/env.go
@@ -41,14 +41,31 @@ var (
 	isAgentuityEnv  = regexp.MustCompile(`(?i)AGENTUITY_`)
 )
 
-func loadEnvFile(le []env.EnvLine, forceSecret bool) (map[string]string, map[string]string) {
+func descriptionLookingLikeASecret(description string) bool {
+	if description == "" {
+		return false
+	}
+	val := strings.ToLower(description)
+	if strings.Contains(val, "secret") {
+		return true
+	}
+	if strings.Contains(val, "password") {
+		return true
+	}
+	if strings.Contains(val, "key") {
+		return true
+	}
+	return false
+}
+
+func loadEnvFile(le []env.EnvLineComment, forceSecret bool) (map[string]string, map[string]string) {
 	envs := make(map[string]string)
 	secrets := make(map[string]string)
 	for _, ev := range le {
 		if isAgentuityEnv.MatchString(ev.Key) {
 			continue
 		}
-		if looksLikeSecret.MatchString(ev.Key) || forceSecret {
+		if looksLikeSecret.MatchString(ev.Key) || forceSecret || descriptionLookingLikeASecret(ev.Comment) {
 			secrets[ev.Key] = ev.Val
 		} else {
 			envs[ev.Key] = ev.Val
@@ -57,25 +74,32 @@ func loadEnvFile(le []env.EnvLine, forceSecret bool) (map[string]string, map[str
 	return envs, secrets
 }
 
-func promptForEnv(logger logger.Logger, key string, isSecret bool, localenv map[string]string, osenv map[string]string) string {
+func promptForEnv(logger logger.Logger, key string, isSecret bool, localenv map[string]string, osenv map[string]string, defaultValue string, placeholder string) string {
 	prompt := "Enter the value for " + key
 	var help string
-	var defaultValue string
 	var value string
 	if isSecret {
 		prompt = "Enter the secret value for " + key
 		if val, ok := localenv[key]; ok {
 			help = "Press enter to set as " + maxString(cstr.Mask(val), 30) + " from your .env file"
-			defaultValue = val
+			if defaultValue == "" {
+				defaultValue = val
+			}
 		} else if val, ok := osenv[key]; ok {
 			help = "Press enter to set as " + maxString(cstr.Mask(val), 30) + " from your environment"
-			defaultValue = val
+			if defaultValue == "" {
+				defaultValue = val
+			}
 		} else {
 			help = "Your input will be masked"
 		}
 		value = tui.Password(logger, prompt, help)
 	} else {
-		value = tui.Input(logger, prompt, help)
+		if placeholder == "" {
+			value = tui.InputWithPlaceholder(logger, prompt, placeholder, defaultValue)
+		} else {
+			value = tui.InputWithPlaceholder(logger, prompt, help, defaultValue)
+		}
 	}
 
 	if value == "" && defaultValue != "" {
@@ -141,7 +165,7 @@ Examples:
 		setFromFile, err := cmd.Flags().GetString("file")
 		if setFromFile != "" {
 			if sys.Exists(setFromFile) {
-				le, _ := env.ParseEnvFile(setFromFile)
+				le, _ := env.ParseEnvFileWithComments(setFromFile)
 				envs, secrets = loadEnvFile(le, forceSecret)
 				if len(envs) > 0 || len(secrets) > 0 {
 					hasSetFromFile = true
@@ -227,7 +251,7 @@ Examples:
 				}
 			}
 			if value == "" {
-				value = promptForEnv(logger, key, isSecret, localenv, osenv)
+				value = promptForEnv(logger, key, isSecret, localenv, osenv, "", "")
 			}
 		}
 		if key != "" && value != "" {
diff --git a/go.mod b/go.mod
index 28f5398d..fd335441 100644
--- a/go.mod
+++ b/go.mod
@@ -4,7 +4,7 @@ go 1.24.2
 
 require (
 	github.com/Masterminds/semver v1.5.0
-	github.com/agentuity/go-common v1.0.59
+	github.com/agentuity/go-common v1.0.60
 	github.com/agentuity/mcp-golang/v2 v2.0.2
 	github.com/bep/debounce v1.2.1
 	github.com/bmatcuk/doublestar/v4 v4.8.1
diff --git a/go.sum b/go.sum
index efc4f535..193d1076 100644
--- a/go.sum
+++ b/go.sum
@@ -9,8 +9,8 @@ github.com/Microsoft/go-winio v0.6.2 h1:F2VQgta7ecxGYO8k3ZZz3RS8fVIXVxONVUPlNERo
 github.com/Microsoft/go-winio v0.6.2/go.mod h1:yd8OoFMLzJbo9gZq8j5qaps8bJ9aShtEA8Ipt1oGCvU=
 github.com/ProtonMail/go-crypto v1.1.5 h1:eoAQfK2dwL+tFSFpr7TbOaPNUbPiJj4fLYwwGE1FQO4=
 github.com/ProtonMail/go-crypto v1.1.5/go.mod h1:rA3QumHc/FZ8pAHreoekgiAbzpNsfQAosU5td4SnOrE=
-github.com/agentuity/go-common v1.0.59 h1:WOR35IDV6X7qSBr+E7ztF1PygENO305/nEKd+rDAX2A=
-github.com/agentuity/go-common v1.0.59/go.mod h1:cy1EPYpZUkp3JSMgTb+Sa3sLnS7vQQupj/RwO4An6L4=
+github.com/agentuity/go-common v1.0.60 h1:r9uLZrYnNasnVxsTGju7ktP9+A5D3j13ald8H3Z7AMQ=
+github.com/agentuity/go-common v1.0.60/go.mod h1:cy1EPYpZUkp3JSMgTb+Sa3sLnS7vQQupj/RwO4An6L4=
 github.com/agentuity/mcp-golang/v2 v2.0.2 h1:wZqS/aHWZsQoU/nd1E1/iMsVY2dywWT9+PFlf+3YJxo=
 github.com/agentuity/mcp-golang/v2 v2.0.2/go.mod h1:U105tZXyTatxxOBlcObRgLb/ULvGgT2DJ1nq/8++P6Q=
 github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be h1:9AeTilPcZAjCFIImctFaOjnTIavg87rW78vTPkQqLI8=
diff --git a/internal/deployer/deployer.go b/internal/deployer/deployer.go
index 2bcbaf39..7040d2cf 100644
--- a/internal/deployer/deployer.go
+++ b/internal/deployer/deployer.go
@@ -13,7 +13,7 @@ import (
 
 type EnvFile struct {
 	Filepath string
-	Env      []env.EnvLine
+	Env      []env.EnvLineComment
 }
 
 func (e *EnvFile) Lookup(key string) (string, bool) {
@@ -41,7 +41,7 @@ type PromptHelpers struct {
 	// Ask will ask the user for input and return true (confirm) or false (no!)
 	Ask func(logger logger.Logger, title string, defaultValue bool) bool
 	// PromptForEnv is a helper for prompting the user to get a environment (or secret) value. You must do something with the result such as save it.
-	PromptForEnv func(logger logger.Logger, key string, isSecret bool, localenv map[string]string, osenv map[string]string) string
+	PromptForEnv func(logger logger.Logger, key string, isSecret bool, localenv map[string]string, osenv map[string]string, defaultValue string, placeholder string) string
 }
 
 type DeployPreflightCheckData struct {