diff --git a/cmd/add.go b/cmd/add.go
index 7057252..92fc06d 100644
--- a/cmd/add.go
+++ b/cmd/add.go
@@ -4,53 +4,87 @@ package cmd
 
 import (
 	"fmt"
+	"os"
 
 	"github.com/Ibotta/sopstool/fileutil"
 	"github.com/Ibotta/sopstool/sopsyaml"
 	"github.com/spf13/cobra"
 )
 
-// addCmd represents the add command
 var addCmd = &cobra.Command{
-	Aliases: []string{"a", "encrypt"},
-	Use:     "add [files ...]",
-	Short:   "add file to the encryption list",
-	Long:    `Add files to the list of files managed by sopstool`,
-	Args:    cobra.MinimumNArgs(1),
+	Aliases: []string{"a", "e", "add", "encrypt"},
+	Use:     "add [files ...], add",
+	Short:   "add file to the encryption list and encrypt file. No argument encrypts all in sops config.",
+	Long:    `Add files to the list of files managed by sopstool and encrypt them. If no argument is provided, encrypt everything provided in sops config`,
 	RunE:    AddCommand,
 }
 
 var noEncrypt bool
 var noClean bool
+var forceOverwrite bool
 
 func init() {
 	RootCmd.AddCommand(addCmd)
 
 	addCmd.Flags().BoolVarP(&noEncrypt, "no-encrypt", "n", false, "Do not encrypt the file after adding")
 	addCmd.Flags().BoolVar(&noClean, "no-clean", false, "Do not clean up plaintext after encrypting")
+	addCmd.Flags().BoolVarP(&forceOverwrite, "force", "f", false, "Force overwriting of encrypted files if they already exist")
 }
 
-// AddCommand the command for the add command
 func AddCommand(_ *cobra.Command, args []string) error {
 	initConfig()
 
-	for _, fileArg := range args {
+	if len(args) == 0 && len(sopsConfig.EncryptedFiles) == 0 {
+		fmt.Println("No files specified for encryption and no known encrypted files.")
+		return nil
+	}
+
+	filesToEncrypt := args
+	if len(args) == 0 {
+		filesToEncrypt = sopsConfig.EncryptedFiles
+	}
+
+	encryptedCount := 0
+	for _, fileArg := range filesToEncrypt {
 		fn := fileutil.NormalizeToPlaintextFile(fileArg)
 
-		if fileutil.ListIndexOf(sopsConfig.EncryptedFiles, fn) >= 0 {
-			fmt.Println("Already exists", fn)
-			return nil
+
+		// Check if plaintext file exists on disk
+		if _, err := os.Stat(fn); os.IsNotExist(err) {
+			fmt.Println("Plaintext version of file does not exist:", fn)
+			continue
 		}
 
-		// add file to list
-		sopsConfig.EncryptedFiles = append(sopsConfig.EncryptedFiles, fn)
+		encryptedFilePath := fileutil.NormalizeToSopsFile(fn)
+
+		// Check if encrypted file already exists on disk
+		if _, err := os.Stat(encryptedFilePath); !os.IsNotExist(err) && !forceOverwrite {
+			fmt.Printf("Encrypted version of file %s already exists on disk. Do you want to overwrite it? [y/N]: ", encryptedFilePath)
+			var input string
+			fmt.Scanln(&input)
+			if input == "" || input == "y" || input == "Y" {
+				// Continue with the overwriting process
+			} else {
+				fmt.Println("Skipping:", encryptedFilePath)
+				continue
+			}
+		}
+
+		// Check and add the file to the list if not already present
+		if fileutil.ListIndexOf(sopsConfig.EncryptedFiles, fn) == -1 {
+			sopsConfig.EncryptedFiles = append(sopsConfig.EncryptedFiles, fn)
+			fmt.Println("Added file to encryption list:", fn)
+		} else {
+			fmt.Println("File", fn, "is already in the encryption list.")
+		}
 
-		//if the file exists, encrypt it
+		// Encrypt the file
 		if !noEncrypt {
 			err := encrypter.EncryptFile(fn)
 			if err != nil {
 				return err
 			}
+			encryptedCount++
 		}
 
 		if !noClean {
@@ -58,13 +92,13 @@ func AddCommand(_ *cobra.Command, args []string) error {
 			if err != nil {
 				return err
 			}
+			fmt.Println("Cleaned up plaintext for:", fn)
 		}
 
 		err := sourceCodeManager.AddFileToIgnored(fn)
 		if err != nil {
 			return err
 		}
-		fmt.Println("added file to list:", fn)
 	}
 
 	err := sopsyaml.WriteEncryptFilesToDisk(sopsConfig.Path, sopsConfig.Tree, sopsConfig.EncryptedFiles)
@@ -72,7 +106,7 @@ func AddCommand(_ *cobra.Command, args []string) error {
 		return err
 	}
 
-	fmt.Println("Files added")
+	fmt.Printf("%d file(s) encrypted successfully.\n", encryptedCount)
 
 	return nil
 }
diff --git a/cmd/decrypt.go b/cmd/decrypt.go
index 3a1e2b5..dc2db1e 100644
--- a/cmd/decrypt.go
+++ b/cmd/decrypt.go
@@ -3,6 +3,9 @@
 package cmd
 
 import (
+	"fmt"
+	"os"
+
 	"github.com/Ibotta/sopstool/fileutil"
 	"github.com/spf13/cobra"
 )
@@ -32,13 +35,29 @@ func DecryptCommand(_ *cobra.Command, args []string) error {
 		return err
 	}
 
-	//decrypt all the files
+	decryptedCount := 0 // Counter for successfully decrypted files
+
+	// Decrypt all the files
 	for _, f := range filesToDecrypt {
+		cryptfile := fileutil.NormalizeToSopsFile(f)
+		if _, err := os.Stat(cryptfile); os.IsNotExist(err) {
+			fmt.Println("Encrypted version of file does not exist:", f)
+			// If the encrypted file doesn't exist, skip decryption for this file
+			continue
+		}
+
 		err := encrypter.DecryptFile(f)
-		if err != nil && !allowFail {
-			return err
+		if err != nil {
+			if !allowFail {
+				return err
+			}
+		} else {
+			decryptedCount++ // Increment the counter when decryption is successful
 		}
 	}
 
+	// Print out the total number of decrypted files
+	fmt.Printf("%d files decrypted successfully.\n", decryptedCount)
+
 	return nil
 }
diff --git a/oswrap/exec.go b/oswrap/exec.go
index e60755a..fe50019 100644
--- a/oswrap/exec.go
+++ b/oswrap/exec.go
@@ -46,6 +46,8 @@ func (ew execWrap) RunCommandStdoutToFile(outfileName string, command []string)
 	if err != nil {
 		return err
 	}
+	defer outfile.Close() // Close the file after cmd completes
+	
 	cmd.Stdout = outfile
 
 	err = cmd.Start()