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I create a MailItem like following:

Application outlook = new Application();
NameSpace ns = outlook.GetNameSpace("MAPI");
Inspector inspector;

AutoResetEvent mailSentEvent;

private void Compose()
{
    MailItem mailItem = outlook.CreateItem(OlItemType.olMailItem));
    inspector = mailItem.GetInspector;

    inspector.Display(false);
    ((InspectorEvents_10_Event)inspector).Close += MailItem_Close;

    mailSentEvent = new AutoResetEvent(false);
    mailSentEvent.WaitOne();
}

private void MailItem_Close()
{
    Console.WriteLine("MailItem_Close ...");
    SyncObject syncObject = ns.SyncObjects[1];
    syncObject.SyncEnd += SyncObject_SyncEnd;
    syncObject.Start();
}

private void SyncObject_SyncEnd()
{
    Console.WriteLine("SyncObject_SyncEnd ...");
    mailSentEvent.Set();
}

EDIT After user clicks on Send the output is

MailItem_Close ...
SyncObject_SyncEnd ...

END EDIT

Problem: after the user clicks Send, mail is stuck in outbox when Outlook is not already running before MailItem is created.

As described here, use of SyncObject should avoid this issue. But it doesn't work: when Outlook has not already been running, MailItem is stuck in outbox.

What am I missing? Is it possible at all to ensure mail is being sent if Outlook has not been running in advance?

Abid
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2 Answers2

1

You can use the Start method of the SyncObject class to begin synchronizing a user's folders using the specified Send\Receive group if it is not perfomed automatically. 

Public Sub Sync() 
 Dim nsp As Outlook.NameSpace 
 Dim sycs As Outlook.SyncObjects 
 Dim syc As Outlook.SyncObject 
 Dim i As Integer 
 Dim strPrompt As Integer 
 Set nsp = Application.GetNamespace("MAPI") 
 Set sycs = nsp.SyncObjects 
 For i = 1 To sycs.Count 
Set syc = sycs.Item(i) 
strPrompt = MsgBox( _ 
 "Do you wish to synchronize " & syc.Name &"?", vbYesNo) 
If strPrompt = vbYes Then 
 syc.Start 
End If 
 Next 
End Sub

This problem can occur if the Send immediately when connected option is not enabled, as shown in the following figure from Outlook 2016.

Send immediately

This setting is tied to the following registry data, so this setting can also be configured by an administrator through a modification of the registry.

Key: HKEY_CURRENT_USER\Software\Microsoft\Office\x.0\Outlook\Options\Mail

or

Policy key: HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\x.0\Outlook\Options\Mail

DWORD: Send Mail Immediately
Value: 0

Note In the above registry key paths, x.0 represents the Outlook version (16.0 = Outlook 2016, Outlook 2019 or Outlook for Office 365, 15.0 = Outlook 2013, 14.0 = Outlook 2010, 12.0 = Outlook 2007).

There are a lot of reasons why messages can be stuck in the outbox folder - the Work offline mode is enabled in Outlook, another Outlook process is hanging in memory and etc.

Eugene Astafiev
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  • Thanks, but Send immediately is active in my Outlook installation. So I guess my problem is related to usage of SyncObject. – Abid May 14 '20 at 10:14
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    You will never get the `SyncEnd` event fired if the source object declared in the function. You must prevent the source object from being swiped by the garbage collector. – Eugene Astafiev May 14 '20 at 10:25
  • Even if I declare SyncObject at global level the mail is not being sent and remains in outbox until Outlook is started next time. – Abid May 14 '20 at 10:33
  • Is the Work offline mode enabled in Outlook? – Eugene Astafiev May 14 '20 at 10:41
  • No. Work offline isn't enabled. – Abid May 16 '20 at 09:33
  • see https://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_windows8/imap-emails-getting-stuck-in-outbox/dd7ef716-65ec-47ad-a17d-df563dfc486f – Eugene Astafiev May 16 '20 at 12:23
1

Make sure syncObject variable is declared on the global level, otherwise it will get Garbage Collected.

Also, get rid of the mailSentEvent.WaitOne() - it stops your app, and the event will never fire since it needs the Windows message pump to run.

Dmitry Streblechenko
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