Немного валидации настроек, например, при появлении новой RountToMinutes, делили на 0 и крэш

JiraTimeBotForm/Configuration/Settings.cs

@@ -1,5 +1,7 @@
 using System;
+using System.Collections.Generic;
 using System.IO;
+using System.Linq;
 using System.Windows.Forms;
 using Newtonsoft.Json;
 
@@ -19,6 +21,70 @@ namespace JiraTimeBotForm.Configuration
         public TimeSpan ActivationTime { get; set; }
         public bool AddCommentsToWorklog { get; set; }
 
+        public static Settings LoadAndCheck(Action settingsSource, Action<string> errorMessageReporter)
+        {
+            Settings settings;
+            bool settingsValid;
+
+            do
+            {
+                settings = Load();
+                settingsValid = SettingsIsValid(settings, out var message);
+
+                if (!settingsValid)
+                {
+                    if (!string.IsNullOrEmpty(message))
+                    {
+                        errorMessageReporter(message);
+                    }
+
+                    settingsSource();
+                }
+
+            } while (!settingsValid);
+            
+            return settings;
+        }
+
+        private static bool SettingsIsValid(Settings settings, out string message)
+        {
+            if (settings == null)
+            {
+                message = "Заполните настройки";
+                return false;
+            }
+
+            var errors = new List<string>();
+            message = null;
+
+            if (settings.RountToMinutes == default(int))
+            {
+                errors.Add("Укажите округление времени, например, 10 минут");
+            }
+
+            if (string.IsNullOrEmpty(settings.JiraPassword))
+            {
+                errors.Add("Укажите Password от Jira");
+            }
+
+            if (string.IsNullOrEmpty(settings.JiraUserName))
+            {
+                errors.Add("Укажите UserName от Jira");
+            }
+
+            if (string.IsNullOrEmpty(settings.RepositoryPath) || !Directory.Exists(settings.RepositoryPath))
+            {
+                errors.Add("Укажите RepositoryPath");
+            }
+
+            var hasErrors = errors.Any();
+            if (hasErrors)
+            {
+                message = string.Join(Environment.NewLine, errors);
+            }
+
+            return !hasErrors;
+        }
 
         public static Settings Load()
         {
@@ -29,10 +95,24 @@ namespace JiraTimeBotForm.Configuration
             }
 
             var settingsText = File.ReadAllText(settingsPath);
-            var settings = JsonConvert.DeserializeObject<Settings>(settingsText);
 
-            var password = new PasswordEncryptionClass().Decrypt(settings.JiraUserName, settings.JiraPassword, settings.JiraUrl);
+            Settings settings;
-            settings.JiraPassword = password;
+
+            try
+            {
+                settings = JsonConvert.DeserializeObject<Settings>(settingsText);
+                if (settings == null)
+                {
+                    return null;
+                }
+                var password = new PasswordEncryptionClass().Decrypt(settings.JiraUserName, settings.JiraPassword, settings.JiraUrl);
+                settings.JiraPassword = password;
+            }
+            catch (JsonReaderException)
+            {
+                return null;
+            }
+
             return settings;
         }
 

JiraTimeBotForm/UI/frmMain.Designer.cs

@@ -67,7 +67,6 @@
             // 
             // tmrStart
             // 
-            this.tmrStart.Enabled = true;
             this.tmrStart.Interval = 1500;
             this.tmrStart.Tick += new System.EventHandler(this.tmrStart_Tick);
             // 

JiraTimeBotForm/UI/frmMain.cs

@@ -1,6 +1,6 @@
 using System;
 using System.Collections.Generic;
-using System.IO;
+using System.Net.Configuration;
 using System.Threading;
 using System.Threading.Tasks;
 using System.Windows.Forms;
@@ -25,6 +25,8 @@ namespace JiraTimeBotForm.UI
         private readonly ITrayMenu _trayIcon;
         private CancellationTokenSource _tokenSource;
         private Settings _settings;
+        private readonly Action _settingsWindowShow;
+        private readonly Action<string> _settingsErrorReporter;
 
         private CancellationTokenSource GetTokenSource()
         {
@@ -46,13 +48,19 @@ namespace JiraTimeBotForm.UI
             _trayIcon = _container.Resolve<ITrayMenu>();
             _trayIcon.Create(this);
 
-            _settings = Settings.Load();
-
             _job = _container.Resolve<Job>();
             _log = _container.Resolve<ILog>();
             _tasksProcessors = _container.Resolve<IAllTasksProcessors>();
 
             _controls = new Control[] { txtDummyMode, btnStart, btnMeeting, btnSettings };
+
+            _settingsWindowShow = () =>
+            {
+                var frmSettings = new frmSettings();
+                frmSettings.ShowDialog(this);
+            };
+
+            _settingsErrorReporter = msg => MessageBox.Show(msg, "Загрузка настроек", MessageBoxButtons.OK, MessageBoxIcon.Exclamation);;
         }
 
         private void frmMain_FormClosing(object sender, FormClosingEventArgs e)
@@ -62,7 +70,7 @@ namespace JiraTimeBotForm.UI
 
         public Settings ReadSettingsAndLock()
         {
-            _settings = Settings.Load();
+            _settings = Settings.LoadAndCheck(_settingsWindowShow, _settingsErrorReporter);
             
             LockUnlock(false);
 
@@ -79,9 +87,13 @@ namespace JiraTimeBotForm.UI
             btnCancel.Enabled = !enabled;
             tmrStart.Enabled = enabled;
         }
+
         private void Form1_Load(object sender, EventArgs e)
         {
-            _settings = Settings.Load();
+            _settings = Settings.LoadAndCheck(_settingsWindowShow, _settingsErrorReporter);
+            tmrStart.Enabled = true;
+
+            _log.Info($"Загружен бот для {_settings.JiraUserName}, работаем в {_settings.RepositoryPath}");
         }
 
         private async void btnStart_Click(object sender, EventArgs e)

JiraTimeBotForm/UI/frmSettings.cs

@@ -1,11 +1,4 @@
 using System;
-using System.Collections.Generic;
-using System.ComponentModel;
-using System.Data;
-using System.Drawing;
-using System.Linq;
-using System.Text;
-using System.Threading.Tasks;
 using System.Windows.Forms;
 using JiraTimeBotForm.Configuration;
 
@@ -21,7 +14,10 @@ namespace JiraTimeBotForm.UI
         private void frmSettings_Load(object sender, EventArgs e)
         {
             var settings = Settings.Load();
-            SetSettings(settings);
+            if (settings != null)
+            {
+                SetSettings(settings);
+            }
         }
 
         private void SetSettings(Settings settings)
@@ -64,7 +60,10 @@ namespace JiraTimeBotForm.UI
         {
             var settings = ReadSettingsAndLock();
             settings.Save();
+
             MessageBox.Show("Настройки сохранены.");
+
+            DialogResult = DialogResult.OK;
             this.Close();
         }