Office 365 SMTP sending timeouts

Hi All,

since a week some users complain timeout error when are sending new email via smtp.office365.com (TLS port 587).

The users need to retry some time before sending correctly.

Below the log:

--- DEBUG
--- First sending with error
---
1327449920[7f534dd74100]: SMTP Connecting to: smtp.office365.com
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 220 PR2P264CA0022.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 18 May 2018 14:15:45 +0000
1327449920[7f534dd74100]: SMTP entering state: 14
1327449920[7f534dd74100]: SMTP Send: EHLO [192.168.xx.xx]
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-PR2P264CA0022.outlook.office365.com Hello [8x.9x.xxx.xxx]
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-SIZE 157286400
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-PIPELINING
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-DSN
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-ENHANCEDSTATUSCODES
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-STARTTLS
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-8BITMIME
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-BINARYMIME
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-CHUNKING
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250 SMTPUTF8
1327449920[7f534dd74100]: SMTP entering state: 4
1327449920[7f534dd74100]: SMTP entering state: 21
1327449920[7f534dd74100]: SMTP Send: STARTTLS
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 220 2.0.0 SMTP server ready
1327449920[7f534dd74100]: SMTP entering state: 19
1327449920[7f534dd74100]: SMTP entering state: 14
1327449920[7f534dd74100]: SMTP Send: EHLO [192.168.xx.xx]
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-PR2P264CA0022.outlook.office365.com Hello [8x.9x.xxx.xxx]
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-SIZE 157286400
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-PIPELINING
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-DSN
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-ENHANCEDSTATUSCODES
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-AUTH LOGIN XOAUTH2
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-8BITMIME
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-BINARYMIME
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-CHUNKING
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250 SMTPUTF8
1327449920[7f534dd74100]: SMTP entering state: 4
1327449920[7f534dd74100]: SMTP entering state: 21
1327449920[7f534dd74100]: SMTP auth: server caps 0x30134, pref 0x300, failed 0x0, avail caps 0x100
1327449920[7f534dd74100]: (GSSAPI = 0x800, CRAM = 0x2000, NTLM = 0x4000, MSN =  0x8000, PLAIN = 0x200, LOGIN = 0x100, EXTERNAL = 0x400)
1327449920[7f534dd74100]: trying auth method 0x100
1327449920[7f534dd74100]: SMTP entering state: 15
1327449920[7f534dd74100]: SMTP: MSN or LOGIN auth, step 0
1327449920[7f534dd74100]: SMTP Send: AUTH LOGIN
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 334 VXNlcm5hbWU6
1327449920[7f534dd74100]: SMTP entering state: 13
1327449920[7f534dd74100]: SMTP entering state: 16
1327449920[7f534dd74100]: SMTP AuthLoginStep1() for mass*****.vit*****@*** Email address is removed for privacy ***
1327449920[7f534dd74100]: LOGIN auth
1327449920[7f534dd74100]: Logging suppressed for this command (it probably contained authentication information)
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 334 UGFzc3dvcmQ6
1327449920[7f534dd74100]: SMTP entering state: 18
1327449920[7f534dd74100]: SMTP Login response, code 334
1327449920[7f534dd74100]: SMTP entering state: 17
1327449920[7f534dd74100]: SMTP AuthLoginStep2
1327449920[7f534dd74100]: PLAIN/LOGIN auth, step 2
1327449920[7f534dd74100]: Logging suppressed for this command (it probably contained authentication information)
--- DEBUG
--- SIn step 2 AuthLoginStep2 there is a TIMEOUT after 2 minutes
---
--- Second sending is fine
1327449920[7f534dd74100]: SMTP Connecting to: smtp.office365.com
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 220 MR2P264CA0017.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 18 May 2018 14:20:14 +0000
1327449920[7f534dd74100]: SMTP entering state: 14
1327449920[7f534dd74100]: SMTP Send: EHLO [192.168.xx.xx]
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-MR2P264CA0017.outlook.office365.com Hello [8x.9x.xxx.xxx]
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-SIZE 157286400
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-PIPELINING
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-DSN
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-ENHANCEDSTATUSCODES
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-STARTTLS
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-8BITMIME
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-BINARYMIME
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-CHUNKING
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250 SMTPUTF8
1327449920[7f534dd74100]: SMTP entering state: 4
1327449920[7f534dd74100]: SMTP entering state: 21
1327449920[7f534dd74100]: SMTP Send: STARTTLS
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 220 2.0.0 SMTP server ready
1327449920[7f534dd74100]: SMTP entering state: 19
1327449920[7f534dd74100]: SMTP entering state: 14
1327449920[7f534dd74100]: SMTP Send: EHLO [192.168.xx.xx]
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-MR2P264CA0017.outlook.office365.com Hello [8x.9x.2xx.2xx]
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-SIZE 157286400
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-PIPELINING
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-DSN
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-ENHANCEDSTATUSCODES
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-AUTH LOGIN XOAUTH2
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-8BITMIME
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-BINARYMIME
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250-CHUNKING
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250 SMTPUTF8
1327449920[7f534dd74100]: SMTP entering state: 4
1327449920[7f534dd74100]: SMTP entering state: 21
1327449920[7f534dd74100]: SMTP auth: server caps 0x30134, pref 0x300, failed 0x0, avail caps 0x100
1327449920[7f534dd74100]: (GSSAPI = 0x800, CRAM = 0x2000, NTLM = 0x4000, MSN =  0x8000, PLAIN = 0x200, LOGIN = 0x100, EXTERNAL = 0x400)
1327449920[7f534dd74100]: trying auth method 0x100
1327449920[7f534dd74100]: SMTP entering state: 15
1327449920[7f534dd74100]: SMTP: MSN or LOGIN auth, step 0
1327449920[7f534dd74100]: SMTP Send: AUTH LOGIN
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 334 VXNlcm5hbWU6
1327449920[7f534dd74100]: SMTP entering state: 13
1327449920[7f534dd74100]: SMTP entering state: 16
1327449920[7f534dd74100]: SMTP AuthLoginStep1() for ma****.vit****@*** Email address is removed for privacy ***
1327449920[7f534dd74100]: LOGIN auth
1327449920[7f534dd74100]: Logging suppressed for this command (it probably contained authentication information)
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 334 UGFzc3dvcmQ6
1327449920[7f534dd74100]: SMTP entering state: 18
1327449920[7f534dd74100]: SMTP Login response, code 334
1327449920[7f534dd74100]: SMTP entering state: 17
1327449920[7f534dd74100]: SMTP AuthLoginStep2
1327449920[7f534dd74100]: PLAIN/LOGIN auth, step 2
1327449920[7f534dd74100]: Logging suppressed for this command (it probably contained authentication information)
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 235 2.7.0 Authentication successful target host AM6PR0102MB3271.eurprd01.prod.exchangelabs.com
1327449920[7f534dd74100]: SMTP entering state: 18
1327449920[7f534dd74100]: SMTP Login response, code 235
1327449920[7f534dd74100]: SMTP entering state: 3
1327449920[7f534dd74100]: SMTP Send: MAIL FROM:<mas**.vi***@**.it> BODY=8BITMIME SIZE=5827
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250 2.1.0 Sender OK
1327449920[7f534dd74100]: SMTP entering state: 5
1327449920[7f534dd74100]: SMTP Send: RCPT TO:<fa*****.pe*****@**.it>
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250 2.1.5 Recipient OK
1327449920[7f534dd74100]: SMTP entering state: 6
1327449920[7f534dd74100]: SMTP Send: DATA
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 354 Start mail input; end with <CRLF>.<CRLF>
1327449920[7f534dd74100]: SMTP entering state: 7
1327449920[7f534dd74100]: SMTP entering state: 8
1327449920[7f534dd74100]: SMTP Send: .
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 250 2.6.0 <de6c41cc-xxxx-xxxx-4dc6-xxxx3b519652@**.it> [InternalId=397xxxxx51884, Hostname=AM6PR0102MB3271.eurprd01.prod.xxxxxxx.com] 8668 bytes in 0.711, 11.893 KB/sec Queued mail for delivery
1327449920[7f534dd74100]: SMTP entering state: 9
1327449920[7f534dd74100]: SMTP Send: QUIT
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP entering state: 0
1327449920[7f534dd74100]: SMTP Response: 221 2.0.0 Service closing transmission channel
1327449920[7f534dd74100]: SMTP entering state: 10
1327449920[7f534dd74100]: SMTP entering state: 12
1327449920[7f534dd74100]: SMTP connection error quitting 804b0002, ignoring

Thank you in advance,

Simone Reale

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Hello Simone,

 

From your description, I assume you are not using the Outlook client to send mails out. Can you tell the deatiled information about the mail flow? If they set it as the description in SMTP client Submission? And this issue maybe related to the network, please try it without the work netwrok to check it.

 

Meanwhile, please let the users borwser to https://testconnectivity.microsoft.com/  to test their Office 365 account's Outbound SMTP Email  feature and send us the result for further analysis. Please follow: Click Office 365 tab > Outbound SMTP Email > Next > type the needed information > Perform Test. For privacy concern, I have sent you a Private Message to collect it. You can open your community profile and then click View private message to access it.

 

Regards,

Rudy

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Hi Rudy,

thank you for your help.

We use different client and protocol.

I use Outlook 2016 with MAPI over HTTPS and I don't have any issues.

Other users use Outlook 2003 and Thunderbird to connect to O365 mailbox.

In this case the following configuration is used:

sIMAP4 or sPOP3 : outlook.office365.com

SMTP with TLS: smtp.office365.com on port 587

The issue is with Outlook 2003 and Thunderbird and is locate on different sites.

I asked to my colleagues to do the test you suggest.

I will update asap.

I also asked to Network guys to check Firewall and Proxy.

Thank you,

Simone Reale

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Rudy,

I don't see anymore the private message.

I have the first results with Reverse DNS check and without.

Thank you,

Simone

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Hello Simone,

 

Thanks for your quick reply.

 

For accessing the private message, you can open your forum profile > click View private messages button. Please check it on your side and send us the result there.

 

Meanwhile, from your description, the Office 365 account STMP configuration is correct. So, it may be related the clients themselves. Please let the effect users add their Office 365 account to your Outlook 2016 client with the Autodiscover way to check if this issue persist? And for the Thunderbird, please also check if it runs in the latest version.

 

Moreover, is there any update from your network guys?

 

Note: As the Outlook 2003 is too old and it doesn't support any more. For the best usage, it's suggested users update it to the latest Outlook 2016.

 

Regards,

Rudy

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Hello Simone,

Thanks for your private message.

Both the uploaded DNS test result are same with the Outbound test result. Can you check it on your side and upload the DNS records test result again?

Meanwhile, if you can let those users to test their account in an Outlook 2016 client and use the Autodiscover way to configure it to check this issue?

Also, in Thunderbird, please let the user configure Office 365 SMTP server to check this issue as follows:

SMTP server:

smtp.office365.com

port:

587

Authentication method:

normal password

Connectivity Security:

STARTTLS

Regards,

Rudy 

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Hi Rudy,

If I use Outlook 2016 client via MAPI over HTTPs the issue is not present.

I send you my results but the test is green.

Regards,

Simone

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Hello Simone,

 

Yes, I know your Office 365 account works well because your Office 365 for Business is configured via the Autodiscover way. So I need confirm if the effect users' Office 365 account also works well via this way to determine it is the client side or the SMTP server side issue.

 

Meanwhile, have you referred to my latest reply to let those users who use thunderbird reconfigure the Office 365 SMTP server? If not, please try to do it and tell us the result.

 

Moreover, the Outlook 2003 is too old to stop support, can you tell us why they don't change to Outlook 2016? With their Office 365 for Business client, they can easy get the click-to-run Office client. Note: the Office 365 Business Essential doesn't provide the desktop version Office suite.

 

Regards,

Rudy

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Hello Simone,

We appreciate your update for further analysis. Please take your time.

Regards,

Rudy

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Hi Rudy,

we have 9000 E1 O365 licenses and 1000 E3.

The most users use 3th party clients to connect to personal mailbox via Pop3/Imap4/Smtp protocols.

I have configured Thunderbird and I tried to send many mails but no error or warning occurred.

The Reverse Lookup error in "Test Connectivity", I think it is normal. If I use a public internet connection I can't pretend the provide registers the PTR record.

I have just asked to my colleagues an update.

Thank you,

Simone Reale

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 Hello Simone,

Thanks for your information.

May I know if the issue persists when those users update the Outlook 2003 to the latest Outlook 2016? And does the issue persists for those users who use the Thunderbird in the latest version when they tried the STARTTLS connectivity security configuration?

If the issue persists, please see below:

From your description, which Office 365 subscription do those effect users have? If all of them are using Office 365 E3 Subscription? If so, they can download the latest Outlook 2016 and use the Autodiscover service to use their Office 365 account. Can you confirm this scenario?

As we are know, Office 365 E1 plan doesn't provide office desktop client, but we can use it on the web side (OWA). If some of them or all of them are using Office 365 E1 license, may I know if the issue persists on OWA?

And it seems occur on the office 365 authentication process. Can you provide us two or three the effective users' email addresses to check them on our side? Also please provide us the entire mentioned logs for further analysis. If possible, please also send us others error messages if they received from the mail server side. For privacy concern, you can upload them in private message.

Your time is appreciated.

Regards,

Rudy

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Question Info

Last updated September 16, 2020 Views 12,129 Applies to: