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chasg · Apr 12, 2009, 07:18 AM

Hi All,

I recently had to send a series of high resolution photos to a client who insisted that they come via email (I usually recommend ftp). They were using Windows (what flavour, I don't know), and there were problems getting the photos out of the email for use.

When I send photos via Mail (I usually only use Mail to send low res shots to friends and family), I write my message, and then drag the photos into the message. Mac users have no problem dragging those photos out of the message for use elsewhere.

My Windows-using client wasn't able to de-embed the images for use (no "right click and save elsewhere" etc), and they were pretty annoyed with me (forgetting that I suggested we should use ftp). They even called in their IT guy who was pretty happy to heap the blame on me (while also stating that I did not send high res photos, despite my ensuring that I did with the bottom-right drop down in Mail).

We did end up using ftp (grr).

I now want to know how to format an email in Mail such that a Windows-using receiver can retrieve the high resolution photos and use them elsewhere. I used to use Eudora, and any attachments were not embedded in the email and Windows users had no problems accessing them. How do I do the same thing in Mail?

I tried formatting a message as plain text, but the images still embed as when using rich text, and I fear that I will encounter the same problems (though I'm not sure, as I don't have a Windows-using friend to test).

Can anyone offer suggestions or a solution?

Chas

ghporter · Apr 12, 2009, 08:01 AM

I think there's a seriously large question that needs answering before anyone can help you out. What email program were these clients using? I've seen programs like Outlook and Outlook Express cause problems because of "security" features that block attachments.

It would also be important to know how you have Mail set up, and what settings you have in place. There are preferences for attaching Windows-friendly attachments when attaching files.

chasg · Apr 12, 2009, 02:36 PM

Heya, thanks for the reply.

I'll have to assume that they were using Outlook (being so widespread). I do know that they could _see_ the attachments in the emails, they just couldn't take them out and make those files available elsewhere. Their IT guys weren't any help, supposedly they "tried everything".

These photos were destined for press release (so they were panicking). I was away on another shoot, so I actually ended up having to log in remotely to my desktop using VNC via my iPhone and uploading the files via ftp that way (Jaadu on the 3G iPhone saved my b*tt!).

I have Mail set up to "always send Windows-friendly attachments", and encoding is set to Automatic (we're in the same country, so I doubt that there were encoding differences).

I'd just like to ensure that this isn't a problem in the future :-/

Cheers!

Chas

ghporter · Apr 12, 2009, 04:20 PM

I think this problem is on THEIR end, or at least at your ISP, NOT at your end. Those Mail settings should work fine, and they have for me in the past (I use Entourage because I have it, but it also works cross-platform).

It would probably be a good idea to do a test emailing with any new customer to make sure they can receive attachments AND save 'em.

D'Espice · Apr 12, 2009, 04:43 PM

Next time don't embed images directly into your messages but mail ZIP archives instead.

Cold Warrior · Apr 12, 2009, 05:38 PM

Compose your emails in plain text and they should show as attachments.

jogi · Apr 13, 2009, 05:52 AM

Originally Posted by D'Espice

Next time don't embed images directly into your messages but mail ZIP archives instead.

Second that. Just zip the images up and attach them. The easiest way to get round any mail client problems

besson3c · Apr 13, 2009, 08:00 AM

except for the SMTP server's maximum message size setting, which makes email generally a poor choice for shuttling large files around. The RFC states that this is 10 MB, but this is AFTER encoding, which means that your files need to be smaller than this (5 or 6 MB, I believe).

hab · Apr 13, 2009, 10:52 AM

My company email security strips all email with .zip attachments due to concerns that the zip file may contain an infected application. Hence, to send a .zip file you have to rename with file with a different extension, then instruct the recipient to rename the file back to the .zip extension. All in all, a PITA.

chasg · Apr 14, 2009, 06:46 AM

Great answers everyone, thanks.

@ghporter: thanks for the confirmation. I know that I made the mistake of not ensuring that the mails were plain text, so that might have been a problem. I used Eudora for a lot of years, and only moved to Mail to smooth the various .mac sync'ing issues (I wouldn't use Entourage though, doesn't that make you vulnerable to virii that attack MSoft apps?).

@D'Espice & jogi: good suggestion, much appreciated, though @hab's point about zips being a security risk is important. Zipping is an extra step too (while it's a small one, I try to streamline my processes as much as possible, and an extra step grates on my oh-so-efficient nerves! ;-)

@Cold Warrior: my fault for not doing this in the first place (thanks for the confirmation :-)

@besson3c: yeah, the max size of gateways is the main reason I hate sending photos via email. This particular client wanted 20 or so relatively large jpegs (2-4MB each), so I had to send 20 emails, each with a single image (just to be sure they didn't bounce, I've had "two-image" emails bounce in the past). Quite a repetitive pain in the @ss, especially considering the event ended at 2am and I had to edit and send prior to 8am the next day for press release <grr>.

@hab: thanks for that. Considering how much trouble I had with these guys and their IT people, I wouldn't be the least bit surprised if they had that level of security running.

_So_ much easier if everyone would just use ftp! :-)

Thanks again everyone for your contributions.

Cheers!

Chas

JKT · Apr 16, 2009, 03:40 AM

Another tip - make sure you put all the attachments at the very end of your message. Iirc, this issue arises in Outlook when you put the images within the text of your message and not at the very end (yes, Outlook really is that ****ing dumb).

In 10.5, there is a new menu item that will do this automatically for you (note, you need to have a New Message window open for you to be able to select this option and you need to do it - only once I think, and then it sticks - before you add any images to that new message):

Thorzdad · Apr 16, 2009, 05:54 AM

Personally, if I'm sending large files to clients, I use an online file-transfer service like YouSendIt. That avoids all email issues.

ghporter · Apr 16, 2009, 06:24 AM

Originally Posted by chasg

@ghporter: thanks for the confirmation. I know that I made the mistake of not ensuring that the mails were plain text, so that might have been a problem. I used Eudora for a lot of years, and only moved to Mail to smooth the various .mac sync'ing issues (I wouldn't use Entourage though, doesn't that make you vulnerable to virii that attack MSoft apps?).

No, Entourage and all of Office since about 2003 or so has automatically blocked VBasic scripting by default so you're not at any risk at all. It's just clunky, like Outlook.

chasg · Apr 23, 2009, 08:10 AM

@JKT: many thanks for that pointer (good to know that I wouldn't have to choose that menu item _each_ time :-)

@Thorzdad: I _wish_ this client had been savvy enough to use a file transfer service! (I feel that if I'd suggested it, their collective heads would have exploded). Heck, they had ftp, and didn't even know it.

@ghporter: ah, thanks for that info (old knowledge is dangerous :-/