Original Tip
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Sending Pictures through eBay Messages
For the past year, eBay has allowed pictures to be forwarded through My Messages. This allows buyers and sellers to resolve issues by sharing photos. Many on this forum are unaware of this new eBay feature, which I've used successfully since Spring of 2011 and which is supported by eBay's instructions on this page:
How can I send emails with attachments to a buyer’s My Messages inbox?
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eBay has added this feature to My Messages because they no longer allow members to publish email addresses in listings or to ask members for personal email addresses. This security feature protects anonymity and should lower scamming and trolling.
How it works
No photos here: The first contact between members using eBay messages will not allow attachments. Nor can you use the editor in eBay Messages to attach photos.
Add photos here: Instead, the procedure is to respond to a copy of an eBay message that was passsed to your normal email, and then attach your photo to that response.
Anonymity: The email that you respond to will have an encoded eBay email address for your trading partner, so you will know their eBay name but not their real email address; and, similarly, they will not know your real email address.
No photos here: Your response from your normal email will pass through your My Messages account and a copy will be placed there. A copy will also arrive in your recipient's My Messages box. However, the photo will not be placed in either message box.
Receive photos here: The photo will continue on to the recipent's normal email so that they can view the attached photo there, rather than on eBay.
Audit Trail: Because the information passes through eBay's My Messages, there is an audit trail of the conversation and this can be helpful if eBay needs to mediate a resolution.
Side Note: if you are responding to a request for more photos in an active listing, the better approach is to add more photos to your listing rather than trading photos by email. This will help other potential buyers and could improve bidding on your item.
Limitations
There are some requirements to make this work:
1) You must receive copies of your eBay messages in your normal email (check your spam filter and make corrections if necessary, and make sure your email address is current in your eBay settings — see screenshot below).
2) Your regular email server and software must allow you to accept or attach photos.
3) Your trading partner must receive copies of their eBay messages in their normal email.
4) Their regular email server and software must allow them to accept or attach photos.
5) Size Limits: eBay limits each message to 2MB, so your attached photos must be email-sized and all attachments and comments should not total more than 2MB. That means photos should have a small file size (sized for the web). If necessary, you can send multiple responses to send more photos.
See this Guide if you need help sizing photos for email:
Web Size your photos
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Screenshot — Communications preferences for your eBay messages:
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