Categories: Computer email program (please specify: Apple Mail, Outlook, Thunderbird, etc) :

Outlook 2007 suddenly can't SEND email via SMTP thru gmail

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Outlook 2007 suddenly can't SEND email via SMTP thru gmail bk1537 7/17/10 8:26 PM
Explain your issue in full detail here:

I suddenly can't SEND email via gmail.  I have a number of gmail accounts, and all are experiencing the same problem.  It happened last night, but after playing with a number of settings (and ultimately resetting the same values), it was corrected...for 1 day.
 
Now it's back, and no amount of resetting the correct (per the gmail Settings page) values is bringing it back.
 
As indicated below, I just changed from Trend Micro to Avast for antivirus software.  I tried disabling the email review, but that still didn't change anything.
 
Operating system:  Windows 7 for at least 6 months: 
Program and version you use to access Gmail:  Outlook 2007  
Your antivirus software just changed to Avast (was Trend Micro)
Any extensions, toolbars or plug-ins:  None that I'm aware of
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail KeithR 7/24/10 11:28 PM
Have you tried signing in to Gmail using the web interface?  Doing that can often provide extra information.
How often does Outlook check for new mail?  If you check too often, Gmail can reject connections.
You might benefit from the Clear Captcha process.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail Jbb0906 8/8/10 12:36 AM
I am also having the same problem. Until 6 months ago or so, this has never been a problem, however, it was with yahoo, which is why I stopped using Yahoo...!

I am using Mac OSX and Mail, but I experience the same problem using Thunderbird. As well as my smartphone. Mail checks for mail ever 10 minutes and has always been set to do that. i receive mail with no problems. I just can´t reply or send new messages. When I do, I get a message that the SMTP server is not set correctly. Eventually, things go back to working normally, with no intervention, but this can take from 1 day to 2 weeks.

It is never predictable and sometimes after an hour or so, the message will actually go through.
Using the Clear Captcha process has no effect. My only option so far has been to simply use the web interface, which defeats the purpose of having a mail reader.

I understand that Google periodically updates their "certificate" and this seems to be the time when I have a problem, but in none of my software, can I find the place to update it on my system. The only thing that seems to work consistently is to delete and re-add the Gmail account to my mail program.

Maybe someone could suggest to Google that they stop changing what is working. Until then, any help on alleviating this frequent and extremely annoying problem would be greatly appreciated.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail jlua001 8/8/10 3:16 AM
Exactly the same problem here.  I won't repeat, because I am experiencing the same issues as jbb0906, and many others, except that even re-creating the gmail account won't work.  Web access works fine.   The problem comes and goes, so it can't be my Outlook Gmail settings, since, if they were wrong, they would never work.

I think that the problem lies in Google Mail, not anywhere else, and what jbb0906 says as suspect makes sense.  Google, please fix it, because this is a critical malfunction.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail docchild 9/1/10 11:05 AM
I just had 25 time-sensitive documents that gmail says they got sent, but the other party never received them. Potential impact in the thousands of dollars.
 
Can anyone suggest a secure alternative that is not gmail? If google can't fix the problem, time to look elsewhere.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail KeithR 9/1/10 4:07 PM
@docchild, were you using Outlook via Gmail SMTP?
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail Jbb0906 9/1/10 8:41 PM
FINALLY! THO ORACLE SPEAKS! DIDN'T READ THE HEADER, BUT THE SPEAK!

Please forgive the cynicism, but if you will look back through the help request, you can see this has been a persistent problem about which Google has been silent for more than a year!

Yes, as per the subject header, the settings were exactly as defined in the google support documents.

There is nothing wrong with the software settings because it works some days, then on other days, just stops and says that the SMTP server connection failed.

Likewise, it is not specific to Outlook. On multiple computers, it does the same thing, but not necessarily on the same days, on Outlook 2007 under windows 7, Thunderbird under Ubuntu 10.X and Thunderbird and Mail under OSX. It is also "update independent." I am running the latest stable release of all of these OS's but the problem has remained before and after the updates.

It seems that there is an issue with Google constantly updating certificates, but in most of the above OS's and mail readers, I never have an option to update the certificate. The only USUALLY functioning solution is to delete the email account and set it up again.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail KeithR 9/1/10 11:28 PM
@Jbb0906, my post was addressed to @docchild.  If you were to read a few other threads on this forum, you would notice that posts beyond the original question often have nothing to do with the heading, so your sarcasm is wasted.  While your post was clearly about using SMTP, @docchild mentioned Gmail's sent records, so I suspect that the problem is not with SMTP.  I need clarification on that before providing any help.  

Re your issue, I don't believe that certificates have anything to do with it, but you could be correct.  I use Outlook only to download a backup of my messages so I cannot comment further on SMTP problems.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail docchild 9/2/10 12:32 AM
@KeithR, no, I have never used Outlook, I just use Gmail in a Web browser ... sometimes IE, sometimes Firefox. I'm suspecting the problem is a spam filter on the other person's end ... she was forwarding her mail to some sort of handheld. The thing that has me wondering, though, is that I changed my sig file about the same time that she stopped getting the e-mails. Could a cloaked link in the sig file change the behavior of Gmail or the spam filter on her end? Or could a couple of dozen short e-mails to the same address trigger some sort of block?  I took out my entire sig file for now, so I'll see if that makes a difference, or see if she maybe finds all the e-mails in her spam folder now that she's back in the office.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail KeithR 9/2/10 4:51 AM
It's certainly possible that a spam filter at the receiver could be triggered by a link in a signature.  I would be very surprised if a burst of messages would trigger it unless there was some spammy content involved.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail Mars Creations 12/16/10 8:38 AM

i don't know if i'm too late or waht, but i had same problem now, and all i didi is remove the account setting and set it again,,, i wish if this helpfull

 

Thank you,,,

Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail Yuri771 12/16/10 12:09 PM
I have this same problem for a long while now. I use IMAP with Outlook and on my Windows Mobile phone.

The error message I get sometimes:

Task 'Gmail - Sending' reported error (0x800CCC7D): 'Your outgoing (SMTP) server does not support SSL-secured connections. If SSL-secured connections have worked in the past, contact your server administrator or Internet service provider (ISP).'


Please solve this google. This is getting annoying.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail KeithR 12/16/10 1:54 PM
@Yuri771, please check your Outlook settings and turn off automatic send and receive if it's on.  This setting is intended for POP clients and can confuse the server if it is active when you are using IMAP.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail wb7uxo 12/16/10 2:18 PM
The problem is not with gmail. The problem is with the latest Microsoft update entitled Update for Microsoft Outlook 2007 (KB2412171).  You can fix this by either removing this update or by unchecking the box on the main settings page requiring logon using Secure Password Authentication.  This also works with POP accounts.


Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail KeithR 12/16/10 2:38 PM
The fix offered by @wb7uxo could apply if you are suddenly denied access all the time.  It is not useful if you get occasional errors.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail Jbb0906 12/16/10 10:02 PM
Actually if the problem is with Microsoft update, then it's also with Mac OSX, Linux, Ubuntu, Thunderbird, Spicebird, Outlook, and every other program on the market. It has been an ongoing problem cross-platform for more than a year now. The problem CLEARLY IS with Google. They are either updating certificates or changing something else intermittently, because to fix it, you can delete the account from your email reader and recreate the account, and like magic, it works flawlessly. If Google would at least publish a work around or an explanation, perhaps the tech people among us could work on a permanent fix.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail KeithR 12/16/10 10:36 PM
How could making changes in your email client fix the problem if it was with Google?
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail jlua001 12/17/10 1:07 AM
wb7uxo:

Thank you.  You were absolutely right.  I had started to be unable to logon to Gmail from Outlook 2007.  I uninstalled KB2412171, and it went back to work correctly.  Apparently, I have read that Microsoft is aware of this problem and is working on it, and, on the meanwhile, they have removed this patch from their update list.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail wdurham 12/17/10 2:00 AM
A number of people are reporting difficulties with Outlook today 

The problem appears to be that recent Microsoft updates switched the SPA requirement back on.

This setting needs to be OFF in Outlook for it to work with GMail. GMail does not need Secure Password Authentication as the entire GMail session is already encrypted using SSL. 

Check GMail's instructions for setting up the various flavours of Outlook - 

Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail PamelaB44 12/28/10 2:56 PM
FINALLY... found the answer to this mysterious event.  Suddenly, could not send or receive in Outlook from Gmail account.  I blammed Gmail, then blammed Microsoft Updates.  It was a terrible experience researching my problem.  I tried every resolution people suggested.  I thought, okay, what is the last thing that I changed...  my Antivirus program!
I have Webroot and it is doing a great job but found when I clicked on the PC Security Button, under the "Shields" tab, Network Protection,... my email shield was not checked... when I checked it, "edit options" lit up.  I pressed that and found the port setting were not right.  I put the correct settings for pop3 incoming and smpt outgoing, pressed okay, opened Outlook 2007 for the gazillionth time, and WOW, my email from five days ago, popped right in!
 
Hope this helps those still working on this problem.
Re: Outlook 2007 suddenly can't SEND email via SMTP thru gmail slimster99 1/16/11 4:01 AM
I had the same issue creap up on me after using GMAIL in Outlook for 2 years.  All of a sudden I couldn't send.  Finally I figured it worked by UNchecking "logon using Secure Password Authentication".
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