Failed to send Email: smtp errors

Since purchasing LR 5.6 earlier this year from B&H, I have been unable to email photos. When attempting to do this, I receive the following error message: Failed to send Email, Cannot establish a secure channel with the outgoing email server smtp-mail.outlook.com. Please provide me with detailed instructions re how I can correct this problem. I am using LR 5.6 to process Nikon D800E raw imaged @files on my Dell laptop computer. Except for this problem, LR works fine for me even if it is at times slow.

Similar Messages

Re: Keep getting "Failed to send email" "Server error" on outgoing emails from phone

I'm having the same issue. I'm using wifi, but it won't send from either yahoo or sbcglobal email. This issue started a few days ago.
Message branched as required by the Verizon Wireless Terms of Service
Message was edited by: Admin Moderator

I have a Galaxy Note 3

Keep getting "Failed to send email" "Server error" on outgoing emails from phone

I think this might have to do with blocking of port 25
How do I fix this?

I can understand how frustrating it is to receive errors when trying to check your email kriley1925. Emails are very important to me and I understand how it is needed for contact with friends and family. Let's work on getting this fixed immediately. What phone do you have? What email accounts are you using? Which email account are you having the issue with? Have you check the incoming and outgoing service settings? Have you had any other issues with your device or email? Please keep us posted and I look forward to hearing from you. ^KH

Since updating my macbook air with OS X mavericks i can't send emails smtp account failed my email host is 123reg

since updating my macbook air with OS X mavericks i can't send emails smtp account failed my email host is 123reg any ideas how to sort it out?

I am having the same issue with Media Temple Email.
My problem in more detail is:
Adding my Media Temple Hosted domain email to a desktop service on my Macbook Air.
I have tried this on both Mac Mail and Thunderbird.
I add the account manually and have checked, double checked, triple checked the server addresss and also the user name and password and they are correct.
I have altered the ports from being default to custom and have tried both SSL and non SSL and still it is unable to connect to the SMTP server.
IMAP inbox is working as I recieve mails but can not send them.
I have chatted to Media Temple and they say it must be something to do with the hardware of the MacBook Air which to start with I disagreed with but I have since tried adding the email to my Mac Mini and it works fine.
I am assuming their is an issue in the MacBook Air with the SMTP ports and I would really appreciate some advice on how to fix this as I don't want to use Webmail for ever.
Thanks in Advance

Failed to send email report ,The transport failed to connect to the server

HI i have to automate my report using sub
1.I have configured SMTP server in the configuration settings
2. I have created subscitption using my report,But i here i will found one error.
Please find the
failed to send email report ,The transport failed to connect to the server
and can u please help me out for this
when i check in the loge files it will show this error below
No DSN present in configuration file, Microsoft.ReportingServices.Diagnostics.Utilities.ServerConfigurationErrorException: The report server has encountered a configuration error. ;

I have change the settings as u suggested but still not able to send the mail .
its shows me the same error mesg
<Header>
<Product>Microsoft SQL Server Reporting Services Version 2009.0100.1600.01 ((KJ_RTM).100402-1539 )</Product>
<Locale>English (United States)</Locale>
<TimeZone>W. Europe Standard Time</TimeZone>
<Path>C:\Program Files\Microsoft SQL Server\MSRS10_50.MSSQLSERVEREPORT\Reporting Services\Logfiles\ReportServerService__02_10_2015_03_44_06.log</Path>
<SystemName>WEGDACM1</SystemName>
<OSName>Microsoft Windows NT 6.1.7601 Service Pack 1</OSName>
<OSVersion>6.1.7601</OSVersion>
<ProcessID>10420</ProcessID>
<Virtualization>Hypervisor</Virtualization>
</Header>
rshost!rshost!28d0!02/10/2015-03:44:06:: i INFO: Currently registered url http://+:80/ReportServer_MSSQLSERVEREPORT/ on endpoint 2
rshost!rshost!28d0!02/10/2015-03:44:06:: e ERROR: Failed to register url=http://+:80/Reports/ for endpoint 3, error=b7.
rshost!rshost!28d0!02/10/2015-03:44:06:: w WARN: Endpoint 3 is enabled but no url is registered for vdir=/Reports, pdir=C:\Program Files\Microsoft SQL Server\MSRS10_50.MSSQLSERVEREPORT\Reporting Services\ReportManager.
servicecontroller!DefaultDomain!28f4!02/10/2015-03:44:06:: e ERROR: Error creating HTTP endpoint. System.Runtime.InteropServices.COMException (0x800700B7): Cannot create a file when that file already exists. (Exception from HRESULT: 0x800700B7)
at Microsoft.ReportingServices.HostingInterfaces.IRsUnmanagedCallback.CreateHttpEndpoint(RsAppDomainType application, String[] urlPrefixes, Int32 cPrefixes, String[] hosts, Int32 cHosts, Boolean wildCardPresent, String virtualDirectory, String
filePath, Int32 authType, Int32 logonMethod, String authDomain, String authRealm, Boolean authPersist, Int32 extendedProtectionLevel, Int32 extendedProtectionScenario, Boolean enabled)
at Microsoft.ReportingServices.Library.ServiceAppDomainController.SetWebConfiguration(RunningApplication rsApplication, Boolean enabled, String folder)
rshost!rshost!28d0!02/10/2015-03:44:06:: i INFO: Endpoint 4 is disabled and no url is registered vdir=/ReportServer_MSSQLSERVEREPORT/ReportBuilder, pdir=C:\Program Files\Microsoft SQL Server\MSRS10_50.MSSQLSERVEREPORT\Reporting Services\ReportServer\ReportBuilder.
rshost!rshost!28f4!02/10/2015-03:44:06:: i INFO: Derived memory configuration based on physical memory as 16776696 KB
servicecontroller!DefaultDomain!28f4!02/10/2015-03:44:06:: i INFO: Recycling the service from the default domain
rshost!rshost!28f4!02/10/2015-03:44:17:: i INFO: Application domain type WindowsService statistics: created: 10, unloaded: 10, failed: 0, timed out: 0.
appdomainmanager!DefaultDomain!28f4!02/10/2015-03:44:17:: i INFO: Appdomain:12 WindowsService_10 started.
library!WindowsService_10!28f4!02/10/2015-03:44:17:: e ERROR: Throwing Microsoft.ReportingServices.Diagnostics.Utilities.ServerConfigurationErrorException: No DSN present in configuration file, Microsoft.ReportingServices.Diagnostics.Utilities.ServerConfigurationErrorException:
The report server has encountered a configuration error. ;
servicecontroller!WindowsService_10!28f4!02/10/2015-03:44:17:: e ERROR: Error initializing configuration from the database: Microsoft.ReportingServices.Diagnostics.Utilities.ServerConfigurationErrorException: The report server has encountered a configuration
error.
resourceutilities!WindowsService_10!28f4!02/10/2015-03:44:18:: i INFO: Reporting Services starting SKU: Enterprise
servicecontroller!WindowsService_9!28f4!02/10/2015-03:44:18:: i INFO: Service controller exiting.
appdomainmanager!DefaultDomain!28f4!02/10/2015-03:44:18:: i INFO: Appdomain:11 unregistered.
appdomainmanager!DefaultDomain!28f4!02/10/2015-03:44:18:: i INFO: Appdomain:11 WindowsService_9 unloading.
appdomainmanager!DefaultDomain!e24!02/10/2015-03:44:18:: i INFO: AppDomain:11 0 pending unload(s)
library!WindowsService_10!19f0!02/10/2015-03:44:18:: e ERROR: Throwing Microsoft.ReportingServices.Diagnostics.Utilities.ServerConfigurationErrorException: No DSN present in configuration file, Microsoft.ReportingServices.Diagnostics.Utilities.ServerConfigurationErrorException:
The report server has encountered a configuration error. ;
library!WindowsService_10!19f0!02/10/2015-03:44:18:: e ERROR: ServiceStartThread: Exception caught while starting service. Error: Microsoft.ReportingServices.Diagnostics.Utilities.ServerConfigurationErrorException: The report server has encountered a configuration
error.
library!WindowsService_10!19f0!02/10/2015-03:44:18:: e ERROR: ServiceStartThread: Attempting to start service again...
library!DefaultDomain!1ca8!02/10/2015-10:55:23:: e ERROR: Throwing Microsoft.ReportingServices.Diagnostics.Utilities.ServerConfigurationErrorException: No DSN present in configuration file, Microsoft.ReportingServices.Diagnostics.Utilities.ServerConfigurationErrorException:
The report server has encountered a configuration error. ;
This is my Logfile can u pls go through it and resolve my issue.

MailServiceHelper Failed while sending email java.lang.NullPointerException

Hi guys,
I am trying to send email with Adobe CQ API.
But i am getting a nullpointer exception at this line: MsgGateway.send(htmlEmail);
This is my method that i am using to send.
import com.day.cq.mailer.MessageGateway;
import com.day.cq.mailer.MessageGatewayService;
import javax.mail.internet.InternetAddress;
   public boolean sendHtmlEmail(SlingHttpServletRequest sling,
            String fromMailAdress, List<String> recepientmailAddress,
            String emailSubject, String htmlbodyMail) {
        HtmlEmail htmlEmail = new HtmlEmail();
        List<InternetAddress> emailAddress = new ArrayList<InternetAddress>();
        try {
            for (String recipient : recepientmailAddress) {
                if (!StringUtil.isEmpty(recipient)) {
                    emailAddress.add(new InternetAddress(recipient));
                    log.error(recipient);
            if (!StringUtil.isEmpty(fromMailAdress)) {
                htmlEmail.setFrom(fromMailAdress);
            htmlEmail.setTo(emailAddress);
            htmlEmail.setSubject(emailSubject);
            htmlEmail.setHtmlMsg(htmlbodyMail);
            htmlEmail.setCharset("utf-8");
            MessageGatewayService MsgService = getMessageGateWayService(sling);
            MessageGateway<HtmlEmail> MsgGateway = MsgService.getGateway(HtmlEmail.class);
            MsgGateway.send(htmlEmail);   //nullpointer exception caught here
            return true;
        } catch (Exception e) {
            log.error("Failed while sending email", e);
        return false;
I have checked to ensure the bundle com.day.cq.cq-mail and my own bundle is running .
I am also sure that 'htmlEmail' is not null by retrieving the email subject via .getSubject and it did return me the subject.
I do not understand what is returning the nullpointerexception.
Thanks in advance !

The MessageGateway instance (MessageGateway<HtmlEmail> MsgGateway) is null therby throwing a null pointer.
Instead of instanciating msgGateway as :
MessageGatewayService MsgService = getMessageGateWayService(sling);
MessageGateway<HtmlEmail> MsgGateway = MsgService.getGateway(HtmlEmail.class);
Inject your MessageGateway as:
@Reference
private MessageGateway<HtmlEmail> msgGateway;
and then call send on msgGateway as msgGateway.send(htmlEmail)
~ Aditya

BO2069: failed to send email med.Microsoft outlook

HI ALL,
We have an erro to send a document by sapb1 using Outlook integration BO2069: failed to send email med.Microsoft outlook
If i open the outlook this erro occurs if i close the outllook the documents sends without problem. Is not funcional becase the user needs his outlook open. Icant found information about it.
Could you helple please?
regards.
NANCY HERNANDEZ.

HI GORDON,
I checkt your link and y I´ve aplied all suggestions but i have de same problem. the question is, Is normal that we have to close outlook to work ok with ms outlook integration in sap?. because this error doesnt appear when msoutllok is close. but this is not functional.
i hope your soon support.
Regards
NANCY HERNANDEZ.

Failed to send Email to user root. (90017)Invalid protocol: null

Dear All ,
After having configure the notification i goto the following error when a notification is enable.
Failed to send Email to user root. (90017)Invalid protocol: null
How to fix it
Regards

Thanks for the prompt return
The link you send to me refer to notification with Grid control and there is no feature to perform a test to send an email . Or may me from cli .
How can i check if EC can send an email . On Os level we use sedmail and it work
Tx

After upgrade to 10.10, can't send email (SMTP cert. error). On previous version running on another machine, can still send find. This new version is missing the "Usual Ports" checkbox option. Can someone please help?

I just upgraded to 10.10. On the mail program, one of my accounts is having an issue sending email. I am getting the following error message:
The certificate for this server is invalid.
Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be sent.
But on another machine running Mavericks, I can still continue to send email. The same is try from my iPhone 5S.
On that machine running Mavericks the SMTP is configured as SSL and for "Usual Ports" (25, 465, 587) but THIS OPTION IS MISSING ON THE NEW VERSION. On the new version I have tried configuring the port to 25 and then 465 and 587 with no success. I have used the Network Utility to see if my provider is blocking me -- it is not. I have no third-party software on this machine (anti virus). I can receive email fine. On the new Yosemitie Mail there are new checkbox options of Automatically check my settings and Allow unsecure connections. I tried to uncheck SSL for SMTP but then it says it cannot send securely my passowrd and i need to check the option "Allow to send unsecurely". I did that but the same error message keeps appearing. So I have tried nearly everything I have been able to, all to no avail. Please can somebody help?

Thanks for your reply. Yes, it is a POP account. Incoming mail is fine. My port for incoming is also 110. But the outgoing port should be 587 (or 24, 465 and 587 as on Mavericks' "Usual Ports" option). I am using the same configuration across three different devices and only the machine running Yosemite is having issues. I notice in the new version of Mail there is no longer the "Usual Ports" option. I am not sure this is the culprit or not. But the fact is no matter how I configure it, it will not send mail for these particular servers. I have multiple clients and only one is affected, meaning I can send email from other email addresses (different hosting contracts) on Yosemite but on this one particular one I cannot.

Fail to send email

Hello,
I have took a copy of the SendEmail.java program, compiled it successfully in my local computer.
When sending a email, I fail.
Here is the source :
// File Name SendEmail.java
import java.util.*;
import javax.mail.*;
import javax.mail.internet.*;
import javax.activation.*;
public class SendEmail
   public static void main(String [] args)
      // Recipient's email ID needs to be mentioned.
      String to = "[email protected]";
      // Sender's email ID needs to be mentioned
      String from = "[email protected]";
      // Assuming you are sending email from localhost
      String host = "localhost";
      // Get system properties
      Properties properties = System.getProperties();
      // Setup mail server
      properties.setProperty("maor1", host);
      // Get the default Session object.
      Session session = Session.getDefaultInstance(properties);
      try{
         // Create a default MimeMessage object.
         MimeMessage message = new MimeMessage(session);
         // Set From: header field of the header.
         message.setFrom(new InternetAddress(from));
         // Set To: header field of the header.
         message.addRecipient(Message.RecipientType.TO,
                                  new InternetAddress(to));
         // Set Subject: header field
         message.setSubject("This is the Subject Line!");
         // Now set the actual message
         message.setText("This is actual message");
         // Send message
         Transport.send(message);
         System.out.println("Sent message successfully....");
      }catch (MessagingException mex) {
         mex.printStackTrace();
and I get this error :
C:\java>java SendEmail
com.sun.mail.util.MailConnectException: Couldn't connect to host, port: localhos
t, 25; timeout -1;
nested exception is:
        java.net.ConnectException: Connection refused: connect
        at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2053)
        at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:69
7)
        at javax.mail.Service.connect(Service.java:364)
        at javax.mail.Service.connect(Service.java:245)
        at javax.mail.Service.connect(Service.java:194)
        at javax.mail.Transport.send0(Transport.java:253)
        at javax.mail.Transport.send(Transport.java:124)
        at SendEmail.main(SendEmail.java:48)
Caused by: java.net.ConnectException: Connection refused: connect
        at java.net.DualStackPlainSocketImpl.connect0(Native Method)
        at java.net.DualStackPlainSocketImpl.socketConnect(Unknown Source)
        at java.net.AbstractPlainSocketImpl.doConnect(Unknown Source)
        at java.net.AbstractPlainSocketImpl.connectToAddress(Unknown Source)
        at java.net.AbstractPlainSocketImpl.connect(Unknown Source)
        at java.net.PlainSocketImpl.connect(Unknown Source)
        at java.net.SocksSocketImpl.connect(Unknown Source)
        at java.net.Socket.connect(Unknown Source)
        at java.net.Socket.connect(Unknown Source)
        at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:312)
        at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:236)
        at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2019)
        ... 7 more
Thank you for helping
Meir

Hello,
I understood my mistake.
I wrote :
// Setup mail server
      properties.setProperty("maor1", host);
instead of :
// Setup mail server
      properties.setProperty("mail.smtp.host", host);
Now it works well.
Thank you for helping.
Best regards
Meir

Email: SMTP error 535 5.7.3 Authentication Unsuccessful

I get the following Lookout error when using the Mailer object to send emails:
Email authentication is failed. SMTP error 535 5.7.3 Authentication Unsuccessful
It works just fine from my office location and other locations, but when I run the same program at my customer's location I get the above error.
I had the IT tech at AT&T open up port 25 on my customers internet account. Before she opened up the port, all I would get
is the error: Timeout during connection to SMTP server.
We use our company's SMTP server in the Mailer object, The SMTP requires authentication

Hi Marelise,
For now, I have enabled these accounts, but in such cases, it is recommended to reach out to chat support or submit a ticket to get faster resolution.
Do let me know if you have any question.

Send Email Java Error

Dears,
I have a database package to send an email to an employee, whole package working well except the send mail part, the error raised from java code i used says ( Can't send command to SMTP host No trusted certificate found).
import java.util.*;
import java.io.*;
import javax.mail.*;
import javax.mail.internet.*;
import javax.activation.*;
public class SendMail {
   // Sender, Recipient, CCRecipient, and BccRecipient are
   // commaseparated lists of addresses.
   // Body can span multiple CR/LF-separated lines.
   // Attachments is a ///-separated list of file names.
   public static int Send(String SMTPServer,
                          String Sender,
                          String Recipient,
                          String CcRecipient,
                          String BccRecipient,
                          String Subject,
                          String Body,
                          String ErrorMessage[],
                          String Attachments) {
      // Error status
      int ErrorStatus = 0;
      // Create some properties and get the default Session
      Properties props = System.getProperties();
      //props.put("MyMailingServer", SMTPServer);
      props.put("mail.smtp.starttls.enable", "false");
     // mail.smtp.starttls.enable=false;
props.put("mail.smtp.host", SMTPServer);
props.put("mail.smtp.port", 25);
props.put("mail.smtp.auth", "true");
props.put("mail.smtp.auth", "user");
props.put("mail.smtp.auth", "password");
      Session session = Session.getDefaultInstance(props, null);
      try {
         // Create a message
         MimeMessage msg = new MimeMessage(session);
         // extracts the senders and adds them to the message
         // Sender is a comma-separated list of e-mail addresses as per RFC822
            InternetAddress[] TheAddresses = InternetAddress.parse(Sender);
            msg.addFrom(TheAddresses);
         // Extract the recipients and assign them to the message.
         // Recipient is a comma-separated list of e-mail addresses as per RFC822.
            InternetAddress[] TheAddresses = InternetAddress.parse(Recipient);
            msg.addRecipients(Message.RecipientType.TO,TheAddresses);
         // Extract the Cc-recipients and assign them to the message.
         // CcRecipient is a comma-separated list of e-mail addresses as per RFC822.
         if (null != CcRecipient) {
            InternetAddress[] TheAddresses = InternetAddress.parse(CcRecipient);
            msg.addRecipients(Message.RecipientType.CC,TheAddresses);
         // Extract the Bcc-recipients and assign them to the message.
         // BccRecipient is a comma-separated list of e-mail addresses as per RFC822.
         if (null != BccRecipient) {
            InternetAddress[] TheAddresses = InternetAddress.parse(BccRecipient);
            msg.addRecipients(Message.RecipientType.BCC,TheAddresses);
         // Subject field
         msg.setSubject(Subject);
         // Create the Multipart to be added the parts to
         Multipart mp = new MimeMultipart();
         // Create and fill the first message part
            MimeBodyPart mbp = new MimeBodyPart();
            mbp.setText(Body);
            // Attach the part to the multipart
            mp.addBodyPart(mbp);
         // Attach the files to the message
         if (null != Attachments) {
            int StartIndex = 0, PosIndex = 0;
            while (-1 != (PosIndex = Attachments.indexOf("///",StartIndex))) {
               // Create and fill other message parts;
               MimeBodyPart mbp = new MimeBodyPart();
               FileDataSource fds =
               new FileDataSource(Attachments.substring(StartIndex,PosIndex));
               mbp.setDataHandler(new DataHandler(fds));
               mbp.setFileName(fds.getName());
               mp.addBodyPart(mbp);
               PosIndex += 3;
               StartIndex = PosIndex;
            // Last, or only, attachment file
            if (StartIndex < Attachments.length()) {
               MimeBodyPart mbp = new MimeBodyPart();
               FileDataSource fds = new FileDataSource(Attachments.substring(StartIndex));
               mbp.setDataHandler(new DataHandler(fds));
               mbp.setFileName(fds.getName());
               mp.addBodyPart(mbp);
         // Add the Multipart to the message
         msg.setContent(mp);
         // set the Date: header
         msg.setSentDate(new Date());
         // Send the message
         Transport.send(msg);
      } catch (MessagingException MsgException) {
         ErrorMessage[0] = MsgException.toString();
         Exception TheException = null;
         if ((TheException = MsgException.getNextException()) != null)
           ErrorMessage[0] = ErrorMessage[0] + "\n" + TheException.toString();
           ErrorStatus = 1;
      return ErrorStatus;
   } // End Send Class
} // End of public class SendMail

i changed my smtp server and now i am getting the following error...please help
C:\trainee>java Emailer
Cannot send email. javax.mail.SendFailedException: Invalid Addresses;
nested exception is:
com.sun.mail.smtp.SMTPAddressFailedException: 504 <nb123@tcs05>: Sende
r address rejected: need fully-qualified address
nested exception is:
com.sun.mail.smtp.SMTPAddressFailedException: 504 <nb123@tcs05>: Sende
r address rejected: need fully-qualified address
nested exception is:
com.sun.mail.smtp.SMTPAddressFailedException: 504 <nb123@tcs05>: Sende
r address rejected: need fully-qualified address

Can't send email - smtp sever offline

I can receiver email, but cannot send email. my SMTP server is flagged as offline

We need more info: iMac model? Mac OS version? What program do you use to read e-mail?

Intermittent sending email- no error messages

I have been battling an intermittent email sending issue for about 3 months and here's the scenario. We are using Thunderbird version: 31.5.0 generally with no issues, then without notice we will no longer be able to send emails reliably. I have tried to copy and paste the body of the email to a new email to try to see if that will send, Nope. I am in contact with my email service provider (iPage) trying to see if it is something on their end and in doing that I tried to send the source to a separate computer via a .TXT file and that wouldn't send either. In order to get it to send the source code to the other computer I had to copy and paste it to MS-Word and save it as a .DOC file format. But if we re-type the entire email message and try to re-send it will send with out any issues. Also, the unusual thing that we are seeing is that we are getting the message that the message was sent successfully and there are no errors when the failures are occurring.

Ok if you are being notified the message was sent, that means your providers mail server is telling Thunderbird it got the message with no errors. What it does with it after that is anybodies guess. Except of course the ipage people they have the server and logs to work it out with.
Being locked down to using DOC formats woulds like malware so it can piggy back out on the doc file. Have you run virus scans?
Or it could be that the firewall at the providers end just does not accept TXT attachments. Not all that uncommon. But you would expect them to be able to tell you exactly what their mail rules were.

Mail suddenly refuses to send emails (smtp)

I'm going to have to give up my wonderful Mail program. It just suddenly stopped connecting to my Gmail smtp server about 2 or 3 weeks ago and will not resume. I tried testing the Mail account and it connects to both the Gmail imap and smtp servers just fine but there is something about the authentication process that is jamming outgoing mail.
I looked on the Internet and there are hundreds of other users who've had the same experience and Apple is providing very little response to the problem.
I'm sorry for this. I loved Mail but am forced to go back to the dreaded Microsoft app. ****.
-Don

A-Jay some ISP's block certain ports and it could be one of the ports if not all that mail is trying to use.
Also make sure that each email is using IT'S SMTP server.
Gmail accounts are nearly flawless. It is an IMAP account so I highly suggest just deleting it and readding it.
If the issue persists, try resetting the password for the other email address that is usually the cause for most issues for sending emails. Sometimes you need to select NONE instead of PASSWORD for verification on connection to a SMTP server.
To go to the extreme you can try this but be warned you will lose ALL MAIL AND ALL SAVED MAIL SO ARCHIVE ALL MAILBOXES BEFORE ATTEMPTING:
-Open a finder window
-Go to your Home Folder (your current user folder)
-Double click on library
-Double click on preferences
-find com.apple.mail.plist
-Drag com.apple.mail.plist into the trash
Open mail, add the mail accounts in and see if the issue is resolved. The GMAIL should work like a charm. As for the other, verify your settings with Mac Mail setup assistant:
http://www.apple.com/support/macosx/mailassistant/
That is one of the greatest tools in terms of supporting Mail.

Failed to send Email: smtp errors

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