The issue seemed to be with Ruby 1.9.2 and Paperclip.
I've moved to Ruby 1.8.7 and everything is working fine.

On Nov 5, 11:53 pm, adriaan <[email protected]> wrote:
> My app requires image upload functionality for users to upload
> images.
> I successfully implemented image uploads to S3 using paperclip (as
> outlined in Heroku docs -http://docs.heroku.com/s3). Files are
> processed to generate 2 new image sizes and uploaded to S3.
> This works fine locally, but results in timeouts on Heroku.
>
> So I'm now trying to do the image processing using delayed_job.
> I've tried a few different approaches:
> - using the delayed_paperclip gem  (https://github.com/jstorimer/
> delayed_paperclip)
> -http://madeofcode.com/posts/42-paperclip-s3-delayed-job-in-rails
>
> Both of them led the delayed_job to fail.
>
> Does anyone have / know a good code sample on how to set this up?
> Are there any compatability issues between versions of paperclip and
> delayed_job? (what combination of versions play nice together)
>
> And I was also wondering, if I get te delayed_job is working will
> users still get timeouts on Heroku if it simply takes more than 30
> seconds to upload the image from their local machine to Heroku (before
> image processing)?

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