Problems with Apple Mail attachments not showing in Outlook

I am experiencing problems when using the new Apple Mail 5.0 (with OSX Lion) to send PDF attachments. The recipient using MS Outlook on a PC will see the email, see the attachment icon (paper clip) but they cannot click to open the attachment.
It's like the attachment was stripped off the email.
Any suggestions on how to fix this issue?

I also have this problem, it seems to be something to do with this: http://support.apple.com/kb/TA22343 but I cannot find the "View in Place" or "View as Icon" options. Anyone had any luck?
This however, maybe the cause (with no real solution but to switch to plain text format): http://social.technet.microsoft.com/Forums/en-US/exchangesoftwareupdate/thread/7 98ae640-9091-44c9-b663-63152eb2f0fe/

Similar Messages

Why do Apple Mail attachments not show in SENT?

I use Mountain Lion OSX10.8.2 on a 27" iMac/1TB HD/12GB RAM.
When I write an Apple Mail email and attach a jpg (for example),
I am never sure if the attachment was sent.
Apple Mail will not show me in SENT that there was an attachment.
There is no record of the attachment on the previous sent email.
Am I missing something? How the heck am I suppose to know if
ANY attachment was sent or not?

Hmm I thought this got sorted out in 10.8 but maybe not.
I asume you are in full screen, with the three column view?
If you change to classic you should see the attachment paper clip?
What I had to do for a work-a-round was create a "rule." Even with this you have to right click the selected sent box>> apply rules
Follow throught this thread:
https://discussions.apple.com/thread/3226400?tstart=0

Outlook users' problems with Apple mail attachments

Folks on Windows XP using Outlook 2003 are having problems with email from Apple mail. Apple mail is using Windows Friendly Attachments and Rich Text as the settings. Sometimes attachments (Word, Excel, PDF) come in fine with an additional .htm attachment, but the body text of the message is missing. If the Outlook user opens the .htm file, there is the body of the Apple mail. Testing with Plain Text results in the body text appearing fine in Outlook, but the attachment is seen as a *.dat file and of course can't be opened. The Macs are all on OS X Tiger with all OS updates applied. Users of Outlook in other offices don't have this problem, and users of Thunderbird on Windows don't have this problem. Any ideas on what is causing this and how to resolve it? Is there a setting on Outlook that needs to be tweaked? Is there a setting on Apple mail that needs to be tweaked? Apple mail attachments to this Windows office worked fine until a few weeks ago. I do not know what changed between then and now as I am not in charge of the computers at the Windows office. Could a Mac OS update have caused a problem? Something on Windows or Outlook specifically? Thanks for any help you can provide. I've scoured the web and have tried everything to no avail. Zipping attachments, while a workaround, is not a long-term solution. Thanks!

Is this in an environment where an MS Exchange Server is being used? Seeing a file change to .dat would often point to that.
Plain Text should be the plan of action for users of Apple Mail, but something (probably the Exchange Server) is messing that up. See:
http://support.microsoft.com/kb/138053
and also related:
http://www.pchell.com/support/winmaildat.shtml
Moving to Leopard would probably not solve this -- the administrator of the exchange server must act.
Also the problem with winmail.dat files is known to impact other email clients used even on Windows computers.
Ernie
Message was edited by: Ernie Stamper

Is there a problem with Apple Mail using IMAP

Is there a problem with Apple Mail using IMAP? Having a problem syncing to our mail server: doesn't sync properly when multiple devices use same mail acct. Spoken w/ mail hosting provider who says Apple Mail doesn't follow IMAP protocol properly leaving Apple Mail users to experience a variety of problems when connecting to IMAP accounts. Among them:
- Improper syncing
- Proliferation of drafts during composition of an email.
- Connections on the mail host do not close automatically and proliferate over time until the host rejects further connection requests.
Hosting provider goes on to suggest turning off IDLE command. In my experience turning this feature off did not improve the situation. In fact, it created a few.
Question: Is the hosting provider correct in faulting Apple Mail?
Been fielding the question with a number of people. I'm aware of three people who are experiencing similar problems, each using different mail hosts. Tech reps at inmotionhosting.com and nexcess.com point the finger at a Apple Mail, along with an IT specialist in Los Angeles, CA, and a tech support rep at an Apple Store in Arizona who said that Apple and Google mail are aware of and coordinating to resolve the problem.
Anyone out there have any insights into this?

Is there a problem with Apple Mail using IMAP? Having a problem syncing to our mail server: doesn't sync properly when multiple devices use same mail acct. Spoken w/ mail hosting provider who says Apple Mail doesn't follow IMAP protocol properly leaving Apple Mail users to experience a variety of problems when connecting to IMAP accounts. Among them:
- Improper syncing
- Proliferation of drafts during composition of an email.
- Connections on the mail host do not close automatically and proliferate over time until the host rejects further connection requests.
Hosting provider goes on to suggest turning off IDLE command. In my experience turning this feature off did not improve the situation. In fact, it created a few.
Question: Is the hosting provider correct in faulting Apple Mail?
Been fielding the question with a number of people. I'm aware of three people who are experiencing similar problems, each using different mail hosts. Tech reps at inmotionhosting.com and nexcess.com point the finger at a Apple Mail, along with an IT specialist in Los Angeles, CA, and a tech support rep at an Apple Store in Arizona who said that Apple and Google mail are aware of and coordinating to resolve the problem.
Anyone out there have any insights into this?

Problem with Apple Mail since OSX Mavericks

Hello Folks,
since i've updated my mid-2012 iMac to OSX Mavericks, i have a problem with Apple Mail: When i start the Apple Mail, the program says that it could not connect to the icloud mail server, and that i should enter my icloud passwort. When i do this, everything works fine. But that annoys me, because it worked without any problem under OSX Mountain Lion.
Has anyone an idea what i can do to fix this?
Regards,
Alex

In the iCloud pane of System Preferences, uncheck the box marked Mail and check it again.

Is anyone having problems with apple mail since upgrading to Yosemite?

MacBook Pro 15", mid 2012 running Yosemite 10.10.1 - ever since upgrading to Yosemite, I have a problem with Apple Mail which is that the from address persists on my screen after I close the email. I have to quit mail and sometimes even restart to get rid of it. Has anyone else experienced this? Any ideas?

No, I mean it lingers when I close the email. What I've discovered since I posted earlier is that if I reopen the email and hover over the address in the actual email the one that is persisting goes away. Thank goodness, because it is very annoying. I am wondering if it is somehow intentional in the SW. Thank you for asking.

Problem with Apple Mail and comcast addresses

Sometimes Apple Mail will not let me send to comcast.net addresses, including my own. I get the message: "Cannot send message using the server smtp.comcast.net:[my e-mail address] All other e-mails sends and receives fine. I'm using 10.6.7. What to do?

Thanks, R. Actually, in the current instance, I realized the message would not send simply because it was addressed to an invalid address - I corrected the address and it went out fine, but I wish the program would have told me that was the problem instead of sending me on a wild goose chase about possible server or account setting problems.
I'm still not sure whether this was the case the previous time I had the problem, a day or so, when I was sending a message to multiple addresses (25 or so). There is little way for me to know which of those addresses is or may be invalid.

Problems with Apple Mail and Gmail

Hiya
I'm keen to integrate my Gmail Account with Apple Mail via POP3, however having followed the instructions given by Google - it doesn't seem to work correctly?
I would appreciate if someone would kindly help me. I look forward to hearing from someone.
Many thanks,
Adam

Hi,
I want to setup gmail as the default email.I've tried almost everything..google notifier, don't like to have gmail inbox in my mac apps inbox ( I could do that successfuly ).I hate it actually that I have to use entourage to send photos first to my gmail and then forward to friends.There is nothing wrong with mac mail or entourage but I just love my gmail...help please!
Apple needs to fix two things to make their mail more popular ( infact the features are great especially with new iLife'08 ) : one , mac mail should be free like all major email services ( I'll be happy with 4GB free space rather than 10GB which they are offering now with subscription ) and second they should create userfriendly environment to use any email ids as default.
Thx
C

Problems with certain mail attachments after moving them to a different folder in Mail

I am using Mac Mail as my default email client, and every once in a while when I move a message with an attachment from one folder to another (for example from my Inbox to my Personal folder) in Mail, the attachment will no longer show up, but rather an infinite set of characters.
I know it's a problem with my local Mac Mail client, since:
I can see the attachments perfectly in my webmail
I can see the attachments perfectly in my other Mac's Mail client, as well as on my iPhone and iPad.
This is a sample of what it looks like:
--Apple-Mail-6-682963542
Content-Disposition: inline;
    filename="Opcion 1.png"
Content-Type: image/png;
    x-mac-hide-extension=yes;
    x-unix-mode=0777;
    name="Opcion 1.png"
Content-Transfer-Encoding: base64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 ideas?

Get info on the drive. What format? FAT drives may be behave erratically for heavy-duty use of the kind you are doing. It's okay to leave a flash drive FAT formatted for light use but for heavy-duty file transfer I think you can encounter issues.
iTunes does not look at files directly. It maintains a database (library.itl) of the files in its collection. When you play a track it looks up where that file is located and goes and plays the file in that location. If you manually move a file or folder used by iTunes that database is no longer correct and you get broken links ( ! ). If you want to move files or folders with iTunes you have to let iTunes do it. Since iTunes is organizing your library there isn't much flexibility in what you can do other than move the whole collection to a different folder by changing the media location preference in preferences.
Lion - Disk Utility - https://discussions.apple.com/message/16925522 - repairing your drive using Disk Utility on Lion's recovery partition.

Problem with marking mail as Not Junk in IMAP account

Hi,
I have an IMAP email account on Go Daddy that I forward all my other mail accounts for processing. I use Apple Mail to process this IMAP account and use Mail.app's Junk filter to move Junk mail to the Junk mailbox. This Junk mailbox is mapped in Mail.app to my Go Daddy Bulk Mail IMAP folder, and the Trash and Inbox are also mapped to their respective folders of this IMAP account's Mail.app is set to "Enable junk mail filtering" and "Move it to the junk mailbox".
When junk mail comes in, Mail.app correctly identifies the mail as junk and moves it to the Junk folder. However, if I find a message that Mail.app misidentified as junk and I attempt to mark it as Not Junk, the message gets a Not Junk status (not brown anymore), but the message stays in the Junk folder; Mail.app does not move it back into the Inbox.
I would assume that since both the Inbox and Junk mail (Bulk Mail) folders are IMAP and on the same account, that upon marking the message as Not Junk, this mail should be moved back into the Inbox, just like under POP.
Am I mistaken about the operation of Junk mail under IMAP? Should marking a message as Not Junk move it automatically to the Inbox? Do I have my folders and options set right? Should I possibly use a 3rd party Spam filter such as SpamSieve (where I can control its actions via Applescript)?
Thanks for any info.
Mike

Ah Ernie, I think you found out my "problem".
Before I upgraded to SN, I used SpamSieve to manage my POP SPAM. When I changed to SN, I did away with SpamSieve and POP, and used IMAP and Mail.app's Junk filtering. SpamSieve, since its "Mark As Junk" and "Mark As Not Junk" functionality uses Applescript, it must've moved the Not Junk message back to the inbox.
Thanks for the pointer; I may change back to SpamSieve to get back that functionality.
Mike

SMTP problems with Apple Mail 6.2

Recently my Apple Mail 6.2 has become messed up. It tells me that all my accounts (a gmail, me.com & cloud) are all offline and can not be brought back on line. The Mail on my iPhone and iPad works fine with the exact same settings and exact same accouts that I have had for many months. Something has changed in Mac OS 8 Mountain Lion in release 6.2, IS THIS FIXED?

This is how to solve the problem:
- Open Mail.
- at top left, click Mail, then Preferences.
- Choose the Accounts tab.
- highlight your first mail account on left.
- towards the bottom right, click the arrows on the right side of
'Outgoing Mail Server (SMTP)' and choose the
   ' 'Edit SMTP Server List'
- When the next box opens, click the 'Advanced' tab in the middle right
   of that box.
- choose 'Use custom port:' (2nd choice in middle) and put the
   value 25 in the box on right (i.e. you are forcing Port 25,
    which is the standard port)
- you should be able to 'OK' out of all the boxes, and the SMTP server
   should no longer say Offline.
In 2 out of about 20 Mac's I had to go back in and choose
Use Secure Sockets Layer (SSL) click OK,
then immediately go back and Uncheck the Use SSL box, and click OK again.
In both of those cases I also had to reboot / Restart.
It was probably the 'restart' that got the settings to take hold,
but since I tried checking SSL both times to force the change, I listed it here.
If I had to try with another system, I would skip the SSL step and just reboot.
Port 25 is listed as one of the default ports in choice 1 on the last page;
but it seems like the latest release of Mail for both Lion and Mountain Lion
never really checks port 25.
Like I said, I had to do this with EVERY Mail account after Mail updated to 6.3
in both Lion and Mountain Lion upgrades,
. . . and it worked for all of them. Feel free to ask questions, I'll check back.
Kerry
Message was edited by: homeBased

Problem with Apple Mail and GMail

Can anyone help me with the following problem. I use Apple Mail as my client and GMail iMap as my server. When I create mails I often get a problem (I think caused by the trackpad) where the mouse jumps and I seem to generate a spurious draft email. The result is that I have a mailbox called "All Mail" in the Mail sidebar which contains over 10,000 messages, even though I only have a few hundred real messages (inbox, sent and spam) and my drafts folder is empty. In this mailbox there are numerous versions of the same emails saved during the creation of the email, all slightly different. I just don't understand what is going on.

Hi There
For Gmail setup using apple mail use this guide
http://mail.google.com/support/bin/answer.py?answer=13275
POP access on yahoo accounts is not free. A yahoo mail plus account is needed.
As far as I am aware Hotmail does not allow any POP access at all. I couldn't find any specific information on POP access in Hotmail's help site.
Hope this helps

Verizon changed their mail servers, they say there is a problem with apple mail, how do I fix this?

Verizon changed their email servers. I have tried to change the settings on my imac desktop but having problems sending email. Verizon support could not help, said I should call Apple. Has anyone run into this?

I have had problems with Verizon. I can send and receive emails so not the same issue. But, when I updated the Apple iOS software, it erased my email history on the Verizon server (which I don't really understand how it could do this). The email history is visible in Mail on both my phone and Mac, but when I log into Verizon, it is not there.
Verizon is blaming this on Apple

Outgoing Server Problem with Apple Mail

I have multiple accounts set up in Apple Mail (two IMAP's a gmail and an exchange). The Exchange account receives and sends fine, but the problem is that the Exchange account will not stay listed as the outgoing mail server, despite have it listed as the outgoing server in preferences for that account and is checked as "use only this server." When I try to complse a new message when that account is selected, it defaults to one of the other accounts. I can change in the message to the exchange account and it sends fine. But having to change everytime I send a message is REALLY annoying. Someone please tell me what I'm missing.

Hi
I have a similar problem here i have work accounts which do not need the SSL ticked but when I uncheck the box and in a few seconds the tick is back up again sometimes I have to click about 10 times or so for it to stay off. I tried to do your sollution it did not work on your suggested port but seemed to work on the 25 port . Also I found i only have the problem when I am at work were we are on a PC network and firewall. It seemed to work fine on a normal home line. Also it only happens on Mountain Lion I have a older macbook with snowleopard and there i have not problems sending messages
as right it was said Apple needs to look into that ASAP as it is very frustrating

Problem with Apple Mail To Do

I upgraded to Leopard and all was well until I appended a To Do to a mail message offline. Once I was able to get back online I started receiving the following message:
Some actions taken while the account “RT NODAK” was offline could not be completed online.
Mail has undone actions on some messages so that you can redo the actions while online. Mail has saved other messages in mailbox “Apple Mail To Do” in “On My Mac” so that you can complete the actions while online.
Additional information: The IMAP command “APPEND” (to Apple Mail To Do) failed with server error: APPEND failed: Can't append to mailbox Apple Mail To Do: no such mailbox.
I can click continue and the message will repeat 6 to 7 times and then the application will abort. Also, a mime attachment message will be placed in the Apple Mail To Do folder. I have trashed and deleted the mail message to which I attached the to do but that did not help. I have logged out and into the mail server to no success.
Has anyone else experienced this and if so were you able to solve the problem?

Honestly this has been incredibly agonizing as my world revolves around email. So I hacked away until I figured out a work around.
The way to work around this crashing problem is to create an "Apple Mail To Do" folder in your IMAP account. This might take care of the problem if the server's folder structure is presented as flat (aka no top folder.
If there is a top folder you will need to enter a custom "IMAP Path prefix" indicating the top folder name for the IMAP account that is the focus of the issue. (see "Advanced" under the account settings in prefs) In many cases this prefix will be simply "IMAP". This is the case with the Eudora Internet Mail Server (IEMS).
Afterwords, you should not get the warnings and it should work smoothly. It is still Apple's problem and they need to fix this bug as well as the condition that leads to it by providing a nice user friendly way of identifying the path prefix folder (no, we don't need no stinkin command line tools for real users)

Problems with Apple Mail attachments not showing in Outlook

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