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Julien Pabion
Julien Pabion, Apple Technical Expert
Category: Mac
Satisfied Customers: 10
Experience:  Apple Certified Support Professional macOs 10.12 Sierra - Apple Certified Technical Coordinator - Apple Certified Macintosh Technician - Apple Certified IOS Technician
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I have an issue with Mac Mail using exchange server, I am

Customer Question

Hi, I have an issue with Mac Mail using exchange server
JA: Just to clarify, what's the model of your Mac, and what operating system are you running?
Customer: I am sorry, I don't have the exact details as it is my Boss' computer and at the moment cannot verify anything
JA: What's the model and Operating System (OS) of your device?
Customer: What I can give you the info is that it is iMac running Sierra
JA: When did you purchase your iMac? What troubleshooting have you tried?
Customer: Cannot tell you the version yet
JA: Anything else you want the Mac Expert to know before I connect you?
Customer: The iMac was a few years ago
Submitted: 1 month ago.
Category: Mac
Customer: replied 1 month ago.
The setup:
Client using iMac using Mac Mail
Connection to exchange server 2013
Problem sending email attachments of pictures (jog and png) and resently pdf files also affected.
Customer: replied 1 month ago.
jpg
Expert:  Bhavik Joshi replied 1 month ago.

Hi, I'm Bhavik. Welcome to JustAnswer. I'm reviewing your question now, and will reply back ASAP.

Expert:  Bhavik Joshi replied 1 month ago.

Please let me know what is the exact problem which you are facing while attaching image or pdf files ? Are you getting any error message while doing so ? Try Draging files from the desktop, the Finder, or an app into your message.

Customer: replied 1 month ago.
The recipients sometimes cannot recieve the attachments
Customer: replied 1 month ago.
The computer belongs to my Boss and cannot give access
Customer: replied 1 month ago.
I am using an ipad and was not able to receive the png file, while using a Nokia Windows smartphone can receive the pictures
Expert:  Bhavik Joshi replied 1 month ago.

Do you see a sign like this in your ipad

https://alssl.askleomedia.com/wp-content/uploads/2004/06/image_not_found150.png

Expert:  Bhavik Joshi replied 1 month ago.

To modify the settings on your iPhone to allow images:

  1. Open the settings app.
  2. Select "Mail, Contacts, Calendars."
  3. Set the "Load Remote Images" to ON.

let me know how it goes !!

Customer: replied 1 month ago.
On my ipad, although it said there is an attchments, on the body message there a text in its place " [cid***@******.***
Customer: replied 1 month ago.
The setting on my ipad is correct with load remote images switched ON
Customer: replied 1 month ago.
It seems to work fine when I connect to the server using imap instead of exchange. But there is a reason I need the exchange connection
Customer: replied 1 month ago.
Another test and i received
[cid:16F81F5E-0815-45DB-8357-C7BC2963A4A0] instead of the picture
Expert:  Bhavik Joshi replied 1 month ago.

Try this setting :-

Go to Setting > Mail, Contacts, Calendar > turn OFF Increase Quote Level.

Expert:  Bhavik Joshi replied 1 month ago.

You can change the format of messages you send. Plain text format doesn’t include formatting such as bold or italic text, or items such as tables and images; these messages can be read by all recipients. Rich text format (HTML) can include formatting, tables, and images; these messages may be unreadable for some.

  • Set the format for all messages: Choose Mail > Preferences, click Composing, then choose a message format.

  • Change the format for your current message: Choose Format > Make Rich Text or Format > Make Plain Text before sending the message.

  • Set the format for replies: If you want to use a different format for replies than for other messages you write, choose Mail > Preferences, click Composing, then select “Use the same message format as the original message.”

Expert:  Bhavik Joshi replied 1 month ago.

You need to set Rich Text format (HTML) as a default format for your emails to see the emails. It seems currently it is set as plain text that's why images are not loading.

Customer: replied 1 month ago.
But the same email I received on two different devices and the Windows Mobile I can receive
Customer: replied 1 month ago.
Sending using rich text has the same result
Customer: replied 1 month ago.
Setting of use the same message format as the original message is ticked also.
Expert:  Bhavik Joshi replied 1 month ago.
  1. Click Mail > Preferences.
  2. Click the Viewing button.
  3. Make sure a check mark is next to "Load remote content in messages"
  4. Close the window.
Expert:  Bhavik Joshi replied 1 month ago.

Did this fix your problem ?

Expert:  Bhavik Joshi replied 1 month ago.

If this also doesn't fix your problem then you can try rebuilding your mail box by following below step :-

Mailbox > Rebuild.

When you rebuild mailboxes for IMAP or Exchange accounts, messages and attachments stored on your computer/devices are discarded, and then downloaded again from the mail server to your Mac. Your mailbox appears empty until the download is complete.

Customer: replied 1 month ago.
with regards ***** ***** remote content, the problem is not with the sender iMac. Because we tried sending the mail back to the same sender and the picture is showing
Customer: replied 1 month ago.
Withh regards ***** ***** rebuild, does this really solve the problem of sending out the mail ?
Just to remind you that the receiver is using windows mobile the picture shows, but the receiver using ipad or iphone or other Mac Mail cannot get the attachments
Expert:  Bhavik Joshi replied 1 month ago.

Okay, Yes then rebuild will be of no use.

Expert:  Bhavik Joshi replied 1 month ago.

You are sending emails as rich text or plain text ?

Expert:  Bhavik Joshi replied 1 month ago.

Also try unticking option "Always send Windows-friendly attachments" to see if it is working fine.

Customer: replied 1 month ago.
Tried both rich text and plain text
Customer: replied 1 month ago.
Where is the option for "Always send Windows-friendly attachments". I cannot find this option
Expert:  Bhavik Joshi replied 1 month ago.

From the main Mail window choose Edit > Attachments, then you should see tick mark in Send Windows-Friendly Attachments

Expert:  Bhavik Joshi replied 1 month ago.

Also do this setting change :- From the main Mail window, choose Edit > Attachments > Always Insert Attachments at End of Message.

Customer: replied 1 month ago.
Ok. Trying now
Expert:  Bhavik Joshi replied 1 month ago.

ok.

Customer: replied 1 month ago.
Same result as before
Expert:  Bhavik Joshi replied 1 month ago.

Strange, I am out of ideas now.

Customer: replied 1 month ago.
Just another info, I changed the connection to imap, the picture showed...
But the problem is when the connection is using exchange configuration
Expert:  Bhavik Joshi replied 1 month ago.

Why you do not want to change to IMAP?

Customer: replied 1 month ago.
It works with IMAP setting
Customer: replied 1 month ago.
but there is a problem with the SMTP
Expert:  Bhavik Joshi replied 1 month ago.

I saw below article :-

http://osxdaily.com/2016/12/17/fix-mail-not-showing-attachments-mac/

You can try this out.

Customer: replied 1 month ago.
The exchange server provider does not provide smtp server and therefore must use outside server, which is always problem with connection
Customer: replied 1 month ago.
The problem is the receipient not showing the attachments and not the sender that is not getting the attachments
Expert:  Pete replied 1 month ago.

Hello, I see you have requested a new expert for your question.

What is the total size of all attachments?

Customer: replied 1 month ago.
Hi...
My specific test was 2MB of 2 png file
Expert:  Pete replied 1 month ago.

Do you get any failure message?

Has the recipient checked their junk or spam email folders?

Customer: replied 1 month ago.
Hi Pete,
Sorry for late follow up. There is time difference here.The receipient can receive the email, just that the attachments are missing.
Customer: replied 1 month ago.
Here is the recap:
Sender using iMac with Sierra OS and using Mac Mail with connection to Microsoft Exchange Server 2013.Receipient : Using 2 devices with the same email address, one is an iPad and the other a Nokia with Windows Mobile OS.
The Nokia can receive the pictures while the iPad does not receive and only a message of
[cid:16F81F5E-0815-45DB-8357-C7BC2963A4A0] instead of the picture
Customer: replied 1 month ago.
Note: when I change the sender setup using imap, both receipients receive the pictures, however the drawback is that the SMTP server is only available outside the building and most times there ate problems connecting to it.
Expert:  Pete replied 1 month ago.

Different servers can be set to block and remove different file types.

Are these your own servers?

Can you check their configuration and settings?

Customer: replied 1 month ago.
I have no access to the server.
However, as I ponted out earlier that in the same email sent to the same email address, but open in two different devices produces different results...
Expert:  Pete replied 1 month ago.

But the same email goes through two different email servers, correct?

Customer: replied 1 month ago.
No. One email sent to one email address, but the receipient (me) open the same email in two different devices, one ipad and the other Windows Mobile
Expert:  Pete replied 1 month ago.

Previously you said "The exchange server provider does not provide smtp server and therefore must use outside server"

So there are two different email servers being used - correct?

Customer: replied 1 month ago.
No. What I meant was that the exchange server does not have smtp services and therefore I do not want to use IMAP connection and thus the exchange connection.
Customer: replied 1 month ago.
Do you know the setup of mac mail to an exchange server?
Expert:  Pete replied 1 month ago.

Yes I know the setup of Mac Mail to an Exchange server, however I am not sure what is going on here at all so I will opt out.

Expert:  Julien Pabion replied 1 month ago.

Hi i am Julien and will try to help you on this problem.

Can you erase and reconfigure the exchange account on your iPad and try again ? It can be an simple issue on the iPad.

If this not work I would like that you configure the email address on another iPad or iPhone to check if the problem persist to know if it is from the server or the device that you use.

If the reconfiguration of the account on the iPad solve the problem thank you to rate me 5 stars then i can be paid for my answer to you.

Thank you to let me know anyway the result.

Julien Pabion

Apple Certified Support Professional macOs 10.12 Sierra
Apple Certified Technical Coordinator
Apple Certified Macintosh Technician
Apple Certified IOS Technician

Customer: replied 1 month ago.
Hi Julien,
Let me start again:
The Sender : iMac running OS Sierra, using Mac Mail connection exchange 2013The receiver : iPad OS 10 and Windows Mobile Phone using IMAP connectionThe email : One email from sender with 2 pictures file (png) size 2MB to one email receiver and in iPad the attachments are not showing but in Windows Phone it is showing.
Note: Similar mails have been sent to users and problem opening attachments on iMac OS, iPhone and iPad. But all windows platform is showing. Have not tested on Android.
Customer: replied 1 month ago.
nothing to do with exchange on iPad
Expert:  Julien Pabion replied 1 month ago.

Hi, i understood well thank you, ***** ***** want you to do on the iPad is to delete the account wich is receiving the emails without the attachment and recreate it to see if it does the same issue. To delete the account you go on settings the Mail then go in the account and delete it. You will need the password ***** the email address to recreate it. Thank you to let me know the result.

Expert:  Julien Pabion replied 1 month ago.

So Settings -> Mail -> Accounts -> the account and then Delete at the bottom. After that Settings -> Mail -> Accounts -> Add account

Expert:  Julien Pabion replied 1 month ago.

Then try to receive again on the iPad

Expert:  Julien Pabion replied 1 month ago.

Can you send me the email then i check how i receive it ? My address : XXXXXXXXX also add your email address to send it also to yourself to see if you receive it. Just one precision please did you try to send it to differents address on the same iPad ? Your problem can be from the smtp server which is not a setting in your iPad. Then i will not be able to help you but to understand your problem. Can you send the email to me please ? Thank you

Customer: replied 1 month ago.
Hi Julien,My iPad is working fine as I can receive from other emails with no problems...The problem is with the sender mail as everyone she (My Boss) sends email with picture attachments who uses Mac OS, iPad and iPhone cannot see the attachments.As previously mentioned, if I changed her iMac mail configuration to IMAP connection to the exchange server, my iPad can receive the pictures.What I am asking if there any issues with their Mac mail setup using exchange connection or is there some settings that needs to be done? Attached is the option of exchange connection for the iMac Mail setupAs for sending you an email, I need to ask for My Boss permission to send from her iMac.
Expert:  Julien Pabion replied 1 month ago.

Hi, i understood thank you for explanation.

Then to answer to your question, no, there is no settings to do in Mail to say dont send the attachments so whatever if its a windows or Mac Os or iOs platform if you see the attachent on one of them then it mean that the attachment was sent... And by default your Apple devices should be ok to receive any kinds of attachment in emails so its strange that you saying to me that all the Apple device can not receive it...

There is no reason that iPad (iOs) and Macs (MacOs) will not receive the attachments if the windows receive it.

One reason can be that the files contain malware and are stopped by an antivirus program but why not on windows ? So no i dont think its the reason...

I wanted you to erase the account and recreate it in Mail on the device sending the emails with issue to recreate correctly the smtp server and be sure its not an issue while sending but as i said, if you receive the attachment on other devices it mean that the attachment is correctly sent...

Now to troubleshoot correctly your problem I need to do more tests for understanding.

First I need that you send me an email with the pictures to my address***@******.*** then i can see on my différents devices how it goes. Write "justanswer email test" in the object then i will recognize your email.

I will try to help you to fix your problem as i can but can you please rate me five star from now on the just answer webpage ? Then i will ge paid by justanswer from the money you already paid them already ? If you dont do that they will not pay me... Thank you and i wait for your email for understanding more your problem and help you to fix it.

Customer: replied 1 month ago.
Hi Julien,Ok. I will try ro send you the mail.
In the mean time, how/where do rate ? Is it the Finish button?