Problem sending attachments

I used Mail (and dot-Mac) to send an email with a pdf attachment to a Windoze recipient with an AOL account. The recipient advised me that he was unable to open the attachment. In fact, he indicated that all he saw was my text and a "squiggle." I resent twice with the same results.
I resent again but with Entourage and he received it perfectly.
I used Mail to resend to a different (non-AOL) Windoze recipient and it was received properly.
Any thoughts?
I did confirm that Mail is configured for "Windows-friendly."

The archive made through the Finder will be zip, not StuffIt, so you have no worries about Windows users being able to open it.
As to Entourage, it probably just has something to do with subtle differences in how the attachment is encoded. Someone else could probably give you a more technical answer than that, but basically AOL got something from Mail that it wasn't expecting to see. (Most likely, IMHO, because AOL's software is doing something wrong.)

Similar Messages

Problems sending attachments

Hi,
I've been having constant problems sending MP3 files. I work in music so it's important that this works but it's been steadily getting worse. The average mp3 size for me is around 6.3mb so it's not the file size. The sending bar shows that it gets to about 50% and then an error pops up saying 'Error, This message could not be delivered and will remain in your Outbox until it can be delivered. Sending the message content to the server failed'.
It works occasionally if you quit and restart mail but it really is a pain as I need to send these things constantly. Can any one help?
Cheers
D

Hi MINDERBENDER, and a warm welcome to the forums!
As mentioned, online storage & emailing a link is much better.
A 6.3 MB MP3 may very well be twice that size when sent via eMail, most ISPs/Mail Servers have a limit of 10 MB or less for an email.

Problem Sending attachments with JavaMail API

Hi,
I am able to succesfully able to send the attachment but the body message is not going with it. If i dont send the attachment then the email body goes properly. i can't understand what the problem is . please help.
import java.util.*;
import java.io.*;
import javax.mail.*;
import javax.mail.internet.*;
import javax.activation.*;
import com.sun.mail.smtp.SMTPMessage;
public class Emailer
     String emailSubject = null;
     String emailBody = null;
    String smtphost = null;
     String ccAddr = null;
     String file = "C:\\trainee\\eclipse_lg.gif";
     Vector vecToAddr = null;
     Vector vecCCAddr = null;
     Address fromAddr = null;
public Emailer(Hashtable hashConfigParam) throws Exception
        smtphost = (String)hashConfigParam.get("host");
        ccAddr = (String)hashConfigParam.get("ccAddr");
        vecToAddr = new Vector();
        vecCCAddr = new Vector();
public Boolean setFromAddr(String fromEmailAddr)
          try
               fromAddr = new InternetAddress (fromEmailAddr);
               //if(true)
               //throw new IOException();
          catch (Exception e)
               return null;
     return new Boolean(true);
public Boolean setToAddr(String toEmailAddr)
          try
               for(int j=0; j< vecToAddr.size();j++)
                    if(((String)vecToAddr.get(j)).equals(toEmailAddr))
                         return new Boolean(false);
               vecToAddr.add(toEmailAddr);
               //if(true)
               //throw new IOException();
          catch (Exception e)
               return null;
               return new Boolean(true);
     public Boolean setCCAddr(String ccEmailAddr)
          try
               for(int j=0; j< vecCCAddr.size();j++)
                    if(((String)vecCCAddr.get(j)).equals(ccEmailAddr) && ((String)vecCCAddr.get(j)).equals(ccAddr))
                         return new Boolean(false);
               vecCCAddr.add(ccEmailAddr);
               vecCCAddr.add(ccAddr);
               //if(true)
               //throw new IOException();
          catch (Exception e)
               //System.out.println(e.getClass().getName());
               return null;
          return new Boolean(true);
     public Boolean setEmailSubject(String subject)
          try
               emailSubject = subject;
               if(emailSubject.equals(null))
                    return new Boolean(false);
               else
                    return new Boolean(true);
          catch (Exception e)
               return null;
          //return new Boolean(false);
     public Boolean setEmailBody(String body)
          try
               emailBody = body;
               if(emailBody.equals(""))
                    return new Boolean(false);
               else
                    return new Boolean(true);
          catch (Exception e)
               return null;
          //return new Boolean(false);
public void sendEmail()
       try
            Properties eMailConfigProps = null;
            eMailConfigProps = System.getProperties();
            eMailConfigProps.put("mail.smtp.host", smtphost);
            Session session = Session.getInstance(eMailConfigProps, null);
            MimeMessage message = new MimeMessage(session);
               try
                 message.setFrom(fromAddr);
                  for(int i=0; i< vecToAddr.size(); i++)
                     message.addRecipient(Message.RecipientType.TO,new InternetAddress((String)vecToAddr.get(i)));
                     for(int i=0; i< vecCCAddr.size(); i++)
                      message.addRecipient(Message.RecipientType.CC,new InternetAddress((String)vecCCAddr.get(i)));
                  message.setSubject(emailSubject);
                  //message.setText(emailBody);
                   BodyPart messageBodyPart = new MimeBodyPart();
                    messageBodyPart.setText(emailBody);
                    Multipart multipart = new MimeMultipart();
                    DataSource source = new FileDataSource(file);
                    messageBodyPart.setDataHandler(new DataHandler(source));
                    messageBodyPart.setFileName(file);
                    multipart.addBodyPart(messageBodyPart);
                    message.setContent(multipart);
                    Transport.send(message);
               catch (SendFailedException ex)
                 ex.printStackTrace();
               catch (MessagingException ex)
                 System.err.println("Exception. " + ex);
       catch (Exception e)
            System.out.println(e.toString());
public static void main(String args[])
      Hashtable hash = new Hashtable();
      hash.put("host","213.312.230.211");
      hash.put("ccAddr","[email protected]");
     try
           Emailer objEmailer = new Emailer(hash);
          Boolean fromFlag = objEmailer.setFromAddr("[email protected]");
          String toAddresses = "[email protected]";
          String ccAddresses = "[email protected]";
          Boolean toFlag = objEmailer.setToAddr(toAddresses);
          Boolean ccFlag = objEmailer.setCCAddr(ccAddresses);
          Boolean subjectFlag = objEmailer.setEmailSubject("Emailer.java");
          Boolean bodyFlag = objEmailer.setEmailBody("blah blah blahblha ");
          if((fromFlag.toString()).equals("true") && (toFlag.toString()).equals("true") && (bodyFlag.toString()).equals("true"))
               objEmailer.sendEmail();
     catch(AddressException e)
          e.printStackTrace();
     catch(Exception e)
          e.printStackTrace();

i.e example :
u can do it in this way
MimeBodyPart messageBody = new MimeBodyPart();
messageBody.setText("your message body goes here");
// attaching file i.e make separate object of body part
MimeBodyPart messageBodyPart = new MimeBodyPart();
DataSource source = new FileDataSource(filePath);
messageBodyPart.setDataHandler(new DataHandler(source));
messageBodyPart.setFileName(fileName);
multipart.addBodyPart(messageBody);
multipart.addBodyPart(messageBodyPart);
mimemessage.setContent(multipart);
Transport.send(mimemessage);

Major problems sending attachments from Mail

G'day all,
I frequently have to email colleagues at work from my Mac at home. They all use MS Outlook to view emails.
Whenever I send just an an email (text only) everything comes out fine, my signature etc.
However when i send ANY attachment, e.g .xls .doc or .jpg or any other type the person receiving does not get a regular looking email.
They get 4 files along the top of the page, AT00001.htm, AT00002.htm, the file I sent .xls and one called mylogo.jpg (this is just a little image in my signature).
The "main body" of the email remains empty.
I do tick the 'Windows Friendly box " when sending.
This has been going on for a while apparantly but I was never told.
Any ideas how to overcome this issue as it does look very un-professional when i send emails.
Remember, they are perfect without attachments.

I am having the same sort of issue. I use to be able to attach icon documents in my e-mails. Now attachments are coming up as large documents embedded at the end of the e-mail. I then went to the corner of the e-mail and brought the document down to small size. I just need to attache an icon of the document, not the full document. How do I get this back.

Problem sending attachments in Mail 3.0

Here appears to be yet another bug in Mail 3.0.
If I create a new email, enter in the address, subject and content then try to add an attachment Mail does nothing. It will not attach a file no mater what I do.
However, if I save the email as a draft then reopen it and try attaching again - it attaches the files without a problem.
This is very inconvenient and inefficient and needs to be fixed ASAP.

I understand that there are always issues with new OS releases. My point is that Leopard, altough revolutionary in its addition of new features also broke so many others.
What is perhaps even more disturbing is that there was no warning from Apple about what was going to happen with an upgrade (ie, a new firewall that is OFF by default, until Leopard the firewall was always on by default. New permissions policy that eliminated the 501 group, rendering a user in that group as "unknown" thereby causing all sorts of issues with software, file creation and system access in general).
Sure, there are many improvements in Leopard, but I feel there are also some areas where it has taken a step. In future I will not be one of those scrambling to get the latest release of OSX on my machine!

Difficulty in sending attachments

I am having problems sending attachments, it sits and whirls while displaying a message attaching file. I waited 10 minutes and abandoned it. Tried using various browsers as I wanted the message to come from a particular email address.
Eventually it is saved as a draft but trying to send the draft again results in it just spinning and nothing is sent.
Switched to hotmail which attached and sent it within seconds. (hopefully the recipient will recognise the email comes from me so sent a text message saying to check a mail from my other address. I did not particularly want the recipient to have my hotmail address but had little choice.
I have since tried again by sending it to one of my other BT/Yahoo email addresses with no better success, it was still whirling after one hour.
This was using web mail, I have used a mail server which is actually less helpful as it seems to have sent the message but does not.
Does anyone have any ideas???

I know you have said you have tried various browsers but have you tried it with a "clean" browser with no add ons or ad blockers etc and with the the email in both the "normal" and "basic" view to try and establish if the problem is browser related.

Cannot send attachments in yahoo. Only says "edit attachments" How to send attachments

when I click "attachments" button in an email, it will not let me find one in documents. Just tells me that the button is to edit attachments. Also, attachments in received email will not forward to gmail.

On Thu, 15 Jan 2009 17:06:02 +0000, TAYLORRD wrote:
> Since upgrading from WebAccess 6.5.6 to 7.0.3 we are experiencing
> problems sending attachments. Most small attachments (less than 100KB)
> will send successfully, but larger attachments will not. The compose
> Message screen never clears and the message is not sent. Clicking send
> again repeats this process.
>
> The GW Web Application is running on IIS on Windows 2000 server within
> our DMZ. The failed message attachments appear in the c:\novell\tmp
> directory. We are not using SSL.
>
> The clients are using IE6 or IE7
>
> All other WebAccess functionality is working fine (albeit a little
> slower than 6.5) and are able to open any attachments that are received.
> It sort of seems like a timeout but cannot find any relevant settings.
>
> Has anyone experienced this problem or found a solution?
If this was NetWare I would say that it sounds like a Winsock issue...
There was something about this with the March 08 release of GW7.0.3 but
it was fixed in the 7.0.3 HP1 - which of these two are you using?
HTH

Problem sending attachements with gmail account on mail

Hello:
I have a lot of problems sending attachments with my gmail account using mail.
1. Attachments are not big.
2. I don't have the same problem with other non gmail accounts.
3. When ever I have this problem I go to gamil.com and I am able to send the attachment with no problem.
Any suggestions?
Thanks

No idea ?
Nemrod

Problems with attachments going corrupt from Mail in the dock when sending?

I have had my Mac G5 Tower at home now for a couple of years now and have always had a problem with sending attachments to any one from my .mac account with mail in the dock.
The error massage people would tell they were getting from the files that I attached were (The file is damaged and cold not be repaired). I also tried emailing the same attachment to my self and got the same results.
I always got around this at home by emailing the attachments via web .mac account from apple’s web site this is not an ideal solution.
Using the same .mac account and mail from the dock on my Mac at work no problems at all.
I thought by upgrading from panther to tiger that this would help, I am still having the same trouble.
Can anyone out there help.
Thanks
Mick
Dual 1.8 Ghz PowerPC G5 Mac OS X (10.4.3)

Thank you Justin for your response. Sorry for the delay in responding. I have been unable to log in to my forum account since the first time even though I'd verified my user name, reset the password (everything I could think of). Many hours (literally) on hold with almost every support department at Verizon hasn't resolved the login problem...so I've created a new username with my other email address. I know that creating a new account probably isn't the kosher solution, but my frustration level with Verizon phone suport on this has gone over the top as no one department seems to claim any knowledge of how to help with forum issues and passes me off to somewhere else.
I am using IE 7.0. I only have the problem when I am viewing my emails via the Verizon webmail. When I download the emails to Outlook on my desktop, there are no problems. In webmail, if I have an email showing in the preview pane that has links and I click on that email (in the preview pane), the linked website opens and I can't close it or do anything else. I can't even switch to viewing other emails in my inbox in the preview pane. I can right click on the email showing in the preview pane and select to open in a new window, but if I left click the link activates right there in the preview pane.

If I try to send attachments on my Yahoo email, my iMac freezes up. I don't have the problem with my MacBook Pro.

If I try to send attachments on my Yahoo email, my iMac freezes up. I don't have the problem with my MacBook Pro.

The file format used by the iOS versions of the iWork apps can only be read by the new iWork apps on your Mac - i.e. Keynote 6, Pages 5 & Numbers 3. Those versions for the Mac require Mavericks, OS X 10.9. The "too old" error on a Mac comes if you are trying to open an iWork '08 or earlier file in the newest apps. If you do have the newest apps you can open the files from your iPad.
If you can't or don't want to upgrade to Mavericks & the newest iWork apps your best option would be to export/share the files from the iPad to a type an older version of iWork can read such as Word, text, Excel, etc.
Or contact AppleCare. They made this mess, let them fix it.

Problem sending mail with attachments???

Hi Everybody,
I have got a problem sending mail with attachments...
I am able to send a plain mail ... but when i am trying to send mail along with an attachment ... its not being sent....
its not showing any error it is simply hanging...
what should i do?
If u know any solns please do suggest me....
Thanks in advance

activation.jar is already there...
initially i wrote a swing program as a front end and it was working abs fine... in my sense it was properly sending mails along with the attachments...
when i changed the front-end to JSP handled by Servlets i am getting a problem...
and even the swing program stopped working ...
now swing program is getting compiled but it is hanging at run time showing an exception "Exception occured during event dispatching"
i dont understand what probably may be the problem...
if u can trace out, please give me any suggestions
Thanks in advance and regards

Cannot send attachments in Mail using .mac account, pop account is fine!

Within my Mail.app, I have 2 accounts: one is a .mac account, the other a pop account.
When I send attachments (jpg always and sometimes pdf) with the .mac account, they do not get encoded properly and my recipients cannot view them -- or they can view, say, 10% of the photo.
When I send the same attachments with the pop account, and within the same Mail.app, I do NOT have this problem.
Furthermore, if I send the attachment from my .mac webmail, I do NOT have the problem.
Does Mail.app have a problem with attachments sent via IMAP accounts?
I have tried Repairing Permissions, deleting the outbox.mbx (and emptying the trash).
Does anyone have any other suggestions? This is driving me crazy.
I am running Mail 2.0.5 on Tiger 10.4.3
Thanks a lot in advance, Neil
Long live the sunflower iMac, iBook G4 Mac OS X (10.4)

Hello Neil.
Does Mail.app have a problem with attachments sent via IMAP accounts?
None that I'm aware of.
The Mail.app uses MIME 1.0 for message/attachment encoding (which is the internet standard) for all email accounts.
Is your POP account and the SMTP server used for the account provided by your ISP used for connecting to the internet?
If so, try selecting/using your ISP's SMTP server (the same SMTP server used to send mail via your ISP's POP account) to send mail via your .Mac account as a test.

Problem with attachments and antivirus.scanners

Hi!
Problem is: Sending any attachment from Tiger (10.4.8) mail, all attachments are removed by a virus scanner at receiving end:
This message was modified by F-Secure Anti-Virus E-Mail Scanning.
Tried Windows friendly, text only, repair permissions, sending under other isp etc. no help.
If this same message with same attachment is send from next mac with Panther, it is received ok.
Receiving company is big and wont alter their virus-scanners and the problem clearly lies in Tiger.
Any help welcome.
Mac OS X (10.4.8)

The subject of your message should have been "Problems with attachments and F-Secure antivirus" since this is not a problem with all antivirus software, only with F-Secure.
Check this thread for a possible temporary solution when sending attachments to those who use F-Secure.
http://discussions.apple.com/thread.jspa?messageID=2837384&#2837384

Mail can no longer send attachments

Mail recently lost the ability to send attachments. If I drag an image, PDF, etc. in to the composer, it shows up as an icon with a filename below it, but clicking on the link results in a dialog that says "The file xxx could not be opened because it is empty". Attachments used to just show up inline and send properly. I'm not sure when this behavior started, but I can't seem to get attachments to work any more. Even if I right-click on a JPG and share via email, the attachment created is empty. What's going on?
Thanks,
Scott

Update... I tried all of the recommended solutions for resetting user permissions and ACLs, none of which solved the problem. I finally relented to re-installing the Mountain Lion upgrade and that fixed whatever was keeping Mail from adding attachments. One notable change is that when I was having the problem adding attachments, I would see warnings in the console from sandboxd complaining that Mail was missing file_read_xattr and file_read_data for the files I was trying to attach. Now that attachments work again, I don't see those messages. Perhaps something was hosed with Mails runtime configuration with sandboxd?

Exchange 2007 OWA sends attachments Outlook connector clients cannot send attachments.

Exchange Server 2007 SP1 + Rollup ***Problem with sending email attachments from Outlook 2007***
* Inbound mail arrives in OWA and Outlook normally with and without attachments.
* OWA email to external email account with attachment goes thru successfully.
* Outlook 2007 sends to an external email address with attachments the message does not arrive at the external mailbox. The messages leave Outbox but are never delivered. The messages appear in Sent Items also.
* Outlook sends non attachment emails to external addresses successfully.
* Outlook sends email attachments to local domain accounts fine.
#1 Exchange Server on Server 2013 fully patched problem commences. Exchange Server on version less than first RTM release of Exchange 2007.
#2 Outlook profiles were changed to see if that is the problem.
#3 Upgraded Exchange to SP1 and Rollup 10(Rollup was autodownloaded by MSUpdate)
#4 Ran EXBPA nothing of any interest in the report.
--Unified Messaging not configed (Done nothing)
--SenderID (Re-enabled) I had shut all of the antispam to eliminate these.
-- Junk Store threshold not configed (No change)
Any suggestions to get Outlook clients capable of sending attachments configured.
Thx,
-Scot

Hi Scot,
Providing some information on Poison Queue:
The poison message queue is a special queue that's used to isolate messages that are determined to be harmful to the Exchange system after a transport server or service failure.
The messages may be genuinely harmful in their content and format.
Alternatively, they may be the results of a poorly written agent that has caused the Exchange server to fail when it processed the supposedly bad messages.
The poison message queue is typically empty. If the poison message queue contains no messages it doesn't appear in Queue Viewer or
Get-Queue results. The messages in the poison message queue are never automatically resumed or expired. Messages remain in the poison message queue until they're manually resumed or removed by an administrator.
According to the description above, I suspect Outlook 2007 changed the email's format when send email with attachment. The reason as below:
If the original email's (with attachment) content or format is harmful to the Exchange 2007 server, it will go to the Poison Queue when sending via OWA. However it didn't, sending via OWA is perfect. So I suspect it is an issue on the Outlook 2007
client side.
Please using Pipeline Tracing to verify whether there is something changed during transmission.
More details in the following article:
Using Pipeline Tracing to Diagnose Transport Agent Problems
http://technet.microsoft.com/en-us/library/bb125198(v=exchg.80).aspx
If it is convenient, I suggest doing following tests to narrow down this issue:
Note: Same content, same attachment, same format.
1. Please using Outlook 2010/2013 or others' Outlook clients for testing.
2. Please change to another format for testing. More details in the following article:
Change the message format to HTML, Rich Text, or plain text
http://office.microsoft.com/en-001/outlook-help/change-the-message-format-to-html-rich-text-or-plain-text-HP001232996.aspx
Thanks
Mavis
Mavis Huang
TechNet Community Support

Problem sending attachments

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