Hi Everyone. I'm hoping that someone can help me out here. I'm pretty tech savvy, but I've run into this issue a couple of times and have tried everything I can think of with no resolution.

One of my employees is having a problem sending emails but only to some email addresses, not to all. There has been no similarities in e-mail addresses or anything that I've noticed. (One was a bellsouth.net email, and the other was a company's email) Basically she sends the message and it just hangs in her outbox. I've checked the SMTP settings and everything is correct. She can email most people with no problem. Outlook returns NO errors, it's almost like it thinks that the email was sent, even though it never was. It never gets to her "Sent Items" It basically goes through the "Send/Receive" process and acts like something was sent even tho it never was.

I did try a test where we attempted to send the email and BCC'd her on it, and SHE received it (again, it stayed hung up in the outbox, and never went to "sent") but when we checked with the client, they hadn't received anything.

She's on Outlook 2007, and I'm at a complete loss. Any ideas or advice for things to try would be greatly appreciated.

Kdavis,

The scenario you have described appears to be random. to aid in troubleshooting this issue to find what is causing sent items to hang in the Outbox, please supply some answers to the following questions.

1. What Account type is this user using? ( i.e POP3, IMAP, Exchange)

2. If this is a pop or imap configuration, what is the SMTP port being used and does the SMTP server require authentication?

3. How is this person connected to the internet? Is it a wireless connection? is there evidence that the connection is lost between outlook and the server?

4. Can you PING or TRACERT the recipient domains?

Hope this helps.

In addition to Spider's questions, does this happen even if you start Outlook in Safe Mode? (hold down CTRL while you click the icon) See if this helps: http://www.officeforlawyers.com/outlook/tsol.htm#safe

1. What Account type is this user using? ( i.e POP3, IMAP, Exchange) It's a POP3 account through our domain host for work.

2. If this is a pop or imap configuration, what is the SMTP port being used and does the SMTP server require authentication? The SMTP port being used is 587 because her home internet provider blocks port 25.

3. How is this person connected to the internet? Is it a wireless connection? is there evidence that the connection is lost between outlook and the server? She's connected through the wireless card in her laptop. We don't really have anywhere to hard wire in here at work. There's nothing to support that there's any kind of connection loss because she could send other emails with no problem at the same time these random ones are getting held up in the inbox.

4. Can you PING or TRACERT the recipient domains?I haven't tried that, so let's see what we get. When I ping bellsouth.net, I get request timed out all 4 times. I'll need to get with her to see what the other domain was (she's not in yet today). I know it was some company's URL. I'll check on that today and will get back with y'all on the second address she had problems with.

This is what I got from the TRACERT to bellsouth.net:

Tracing route to bellsouth.net [216.77.188.73]
over a maximum of 30 hops:

1 1 ms 1 ms 1 ms 192.168.1.1
2 41 ms 41 ms 42 ms 99.194.160.1
3 39 ms 40 ms 39 ms j1-rt.fol.gulftel.com [216.231.162.1]
4 56 ms 55 ms 55 ms bb-nlrkargp-jx9-02-ge-0-0-5.core.lightcore.net [
206.51.69.173]
5 61 ms 61 ms 62 ms bb-shptlayo-jx9-02-xe-1-1-0.core.centurytel.net
[206.51.69.29]
6 62 ms 62 ms 65 ms bb-shptlayo-jx9-01-ae0.core.centurytel.net [206.
51.69.61]
7 66 ms 66 ms 66 ms bb-dllstx37-jx9-01-xe-1-1-0.core.centurytel.net
[206.51.69.33]
8 65 ms 66 ms 66 ms bb-dllstx37-jx9-02-ae0.core.centurytel.net [206.
51.69.58]
9 67 ms 65 ms 65 ms te1-1-0d0.cir1.dallas2-tx.us.xo.net [65.47.204.9
]
10 67 ms 66 ms 67 ms 192.205.36.101
11 83 ms 82 ms 82 ms cr1.dlstx.ip.att.net [12.122.195.238]
12 82 ms 82 ms 83 ms cr2.hs1tx.ip.att.net [12.122.28.158]
13 83 ms 81 ms 82 ms cr1.hs1tx.ip.att.net [12.122.5.189]
14 82 ms 81 ms 81 ms cr1.nwrla.ip.att.net [12.122.1.142]
15 178 ms 99 ms 81 ms 12.123.153.17
16 80 ms 115 ms 80 ms 74.175.192.37
17 83 ms 82 ms 84 ms 12.81.24.30
18 82 ms 82 ms 82 ms 12.83.2.190
19 83 ms 82 ms 82 ms 12.83.2.209
20 81 ms 81 ms 81 ms 205.152.152.102
21 * * * Request timed out.
22 * * * Request timed out.
23 * * * Request timed out.
24 * * * Request timed out.
25 * * * Request timed out.
26 * * * Request timed out.
27 * * * Request timed out.
28 * * * Request timed out.
29 * * * Request timed out.
30 * * * Request timed out.




Thanks again for any help.

The second address she was trying to send to is scasurgery.com.

Pinging scasurgery.com [160.109.69.72] with 32 bytes of data:
Reply from 160.109.69.72: bytes=32 time=68ms TTL=242
Reply from 160.109.69.72: bytes=32 time=68ms TTL=242
Reply from 160.109.69.72: bytes=32 time=68ms TTL=242
Reply from 160.109.69.72: bytes=32 time=67ms TTL=242

Ping statistics for 160.109.69.72:
Packets: Sent = 4, Received = 4, Lost = 0 (0% loss),
Approximate round trip times in milli-seconds:
Minimum = 67ms, Maximum = 68ms, Average = 67ms


Tracing route to scasurgery.com [160.109.69.72]
over a maximum of 30 hops:

1 1 ms 1 ms 3 ms 192.168.1.1
2 41 ms 41 ms 40 ms 99.194.160.1
3 40 ms 40 ms 40 ms j1-rt.fol.gulftel.com [216.231.162.1]
4 55 ms 55 ms 57 ms bb-nlrkargp-jx9-02-ge-0-0-5-503.core.lightcore.n
et [206.51.69.173]
5 65 ms 62 ms 61 ms bb-shptlayo-jx9-02-xe-1-1-0.core.centurytel.net
[206.51.69.29]
6 62 ms 61 ms 78 ms bb-shptlayo-jx9-01-ae0.core.centurytel.net [206.
51.69.61]
7 66 ms 66 ms 67 ms bb-dllstx37-jx9-01-xe-1-1-0.core.centurytel.net
[206.51.69.33]
8 65 ms 65 ms 65 ms bb-dllstx37-jx9-02-ae0.core.centurytel.net [206.
51.69.58]
9 65 ms 65 ms 66 ms te1-1-0d0.cir1.dallas2-tx.us.xo.net [65.47.204.9
]
10 66 ms 65 ms 65 ms 0.xe-9-2-0.BR2.DFW13.ALTER.NET [204.255.168.201]

11 66 ms 66 ms 65 ms 0.ge-5-3-0.XL4.DFW7.ALTER.NET [152.63.96.253]
12 92 ms 68 ms 67 ms 0.ge-4-2-0.XT4.DFW9.ALTER.NET [152.63.98.85]
13 88 ms 194 ms 103 ms POS7-0.GW9.DFW9.ALTER.NET [152.63.100.253]
14 67 ms 67 ms 67 ms perot-gw.customer.alter.net [65.208.8.198]
15 67 ms 67 ms 67 ms 160.109.96.11
16 68 ms 69 ms 67 ms KERLANJOBESURGERYCENTER.COM [160.109.69.72]

Trace complete.

Any help is appreciated.

Are you sending thru an SMTP server located on your own network or hosted outside?

Thank you for supplying the PING and TRACERT information as well as the account configuration information.

It does appear there is a security protocol inplace for bellsouth.net. This is very common and is not the cause of the intermittent delay.

When these messages sit in the Outbox unable to send, there can be multiple reasons this is happening. We have eliminated the SMTP server information being correct, the SMTP port being blocked or recipient server experiencing packet lose,

If your SMTP server is in house see if you can locate any traffic logs. This may shed some light on what is causing these delays.

Last possibility is how this user connects to the internet. If connected wirelesslly attempt to troubleshoot connectivity loss between the user and the SMTP server.