diff --git a/pkg/onepassword/client/connect/connect.go b/pkg/onepassword/client/connect/connect.go
index f528e5c..fc967a5 100644
--- a/pkg/onepassword/client/connect/connect.go
+++ b/pkg/onepassword/client/connect/connect.go
@@ -2,7 +2,9 @@ package connect
 
 import (
 	"context"
+	"errors"
 	"fmt"
+	"time"
 
 	"github.com/1Password/connect-sdk-go/connect"
 	"github.com/1Password/connect-sdk-go/onepassword"
@@ -30,7 +32,7 @@ func NewClient(config Config) *Connect {
 func (c *Connect) GetItemByID(ctx context.Context, vaultID, itemID string) (*model.Item, error) {
 	connectItem, err := c.client.GetItemByUUID(itemID, vaultID)
 	if err != nil {
-		return nil, fmt.Errorf("1Password Connect error: %w", err)
+		return nil, fmt.Errorf("GetItemByID 1Password Connect error: %w", err)
 	}
 
 	var item model.Item
@@ -42,7 +44,7 @@ func (c *Connect) GetItemsByTitle(ctx context.Context, vaultID, itemTitle string
 	// Get all items in the vault with the specified title
 	connectItems, err := c.client.GetItemsByTitle(itemTitle, vaultID)
 	if err != nil {
-		return nil, fmt.Errorf("1Password Connect error: %w", err)
+		return nil, fmt.Errorf("GetItemsByTitle 1Password Connect error: %w", err)
 	}
 
 	items := make([]model.Item, len(connectItems))
@@ -55,21 +57,38 @@ func (c *Connect) GetItemsByTitle(ctx context.Context, vaultID, itemTitle string
 	return items, nil
 }
 
+// GetFileContent retrieves the content of a file from a 1Password item.
+// As the Connect has a delay when synchronizing files and returns a 500 error in this case, this function implements a retry mechanism.
 func (c *Connect) GetFileContent(ctx context.Context, vaultID, itemID, fileID string) ([]byte, error) {
-	bytes, err := c.client.GetFileContent(&onepassword.File{
-		ContentPath: fmt.Sprintf("/v1/vaults/%s/items/%s/files/%s/content", vaultID, itemID, fileID),
-	})
-	if err != nil {
-		return nil, fmt.Errorf("1Password Connect error: %w", err)
+	const maxRetries = 5
+	const delay = 1 * time.Second
+
+	var lastErr error
+	for i := 0; i < maxRetries; i++ {
+		bytes, err := c.client.GetFileContent(&onepassword.File{
+			ContentPath: fmt.Sprintf("/v1/vaults/%s/items/%s/files/%s/content", vaultID, itemID, fileID),
+		})
+		if err == nil {
+			return bytes, nil
+		}
+
+		var connectErr *onepassword.Error
+		if errors.As(err, &connectErr) && connectErr.StatusCode == 500 {
+			lastErr = err
+			time.Sleep(delay)
+			continue
+		}
+
+		return nil, fmt.Errorf("GetFileContent 1Password Connect error: %w", err)
 	}
 
-	return bytes, nil
+	return nil, fmt.Errorf("GetFileContent failed after retries: %w", lastErr)
 }
 
 func (c *Connect) GetVaultsByTitle(ctx context.Context, vaultQuery string) ([]model.Vault, error) {
 	connectVaults, err := c.client.GetVaultsByTitle(vaultQuery)
 	if err != nil {
-		return nil, fmt.Errorf("1Password Connect error: %w", err)
+		return nil, fmt.Errorf("GetVaultsByTitle 1Password Connect error: %w", err)
 	}
 
 	var vaults []model.Vault