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I have the following

Item A - $100
Item B - $100
Item C - $100
Item D - $100
Item E - $50

My users are going to buy one of either A, B, C or D

If they buy Item E as well, I'd like to automatically give them a $25 Discount

Is this possible? So, rather than selling the two items for $150 I sell it to them for $125

You could create a separate $125 product (say, Item F) that works as a combo deal, where the buyer would choose from among Items A-D in a dropdown menu (using our "Variations which tell more..." product setting) and get Item E as part of the deal. The cart would show only one item ordered (Item F) at a price of $125 when they Add to Cart, rather than showing Item A/B/C/D and Item E as separate items in the cart.

Another approach would configure a discount code on Item E, good for $25 or 50% off the price of Item E, which you would instruct buyers to type into their cart as a sort of "online coupon" when they also purchase one of Item A-D. However, we presently have no way to enforce that the code would only be applied if Item A-D was also being ordered, so you'd have to be clear about the terms of your offer and manually deal with anyone who orders Item E alone and enters the discount code anyway.

Ok....maybe a slight variation on this question.
So, we have a bundle of most of the items for a discounted price. We currently are hosting a separate zip for this bundle...but it would be great if the bundle button would select all the correct items and then discount the appropriate amount. I think this is the same idea as previously stated, except with a few more items.

Does this seem like something workable in the foreseeable future?

We do have a "package product" feature:
http://www.e-junkie.com/ej/help.package.htm

At present, this only works for download products -- so the package product has its own price and will issue download links for files from any of your other existing download product(s) -- but we may be enhancing this in the future as a way to offer package deals on tangible goods as well.

Guys-

I'm bumping this up as a request for a new feature.

Tyson Another approach would configure a discount code on Item E, good for $25 or 50% off the price of Item E, which you would instruct buyers to type into their cart as a sort of "online coupon" when they also purchase one of Item A-D. However, we presently have no way to enforce that the code would only be applied if Item A-D was also being ordered, so you'd have to be clear about the terms of your offer and manually deal with anyone who orders Item E alone and enters the discount code anyway.

We love e-Junkie but the problem quoted above may be a deal breaker for us.

In short, we offer a package deal, and just before checkout, the customer is offered other products at significant discounts. Anyone with a marginal Google-fu skills could stumble upon our discount page and order items without first buying the package deal.

Yes, we could monitor this, but it would be way easier if there was a button that we could click that says:

"Apply discount only if _____ item is in cart"

With a drop-down of current items in our shop.

I've tried nearly every other variation on here, including a tricky whole-cart discount, but it just doesn't mesh.

Thanks in advance for considering this.

Thanks for the suggestion; I'll assign this to Development for consideration as a new feature on the wishlist. :^)