Great! 

Paperclip 2.7.5 should work. Here's some version pinning I have done for a 
Radiant 1.1.4 on Ruby 1.9.3:

gem "rack-cache", "1.2.0"
gem "rake", "10.4.2"
gem "rdoc", "4.2.0"
gem "radiant", "~> 1.1.4"
gem "compass-rails", "~> 1.0.3"

I don't remember why, but I had 'vendorized' clipped extension, and 
therefore also pinned these:

gem "acts_as_list", "0.1.4"
gem "paperclip",    "~> 2.7.0"
gem "uuidtools",    "~> 2.1.2"
gem "cocaine",      "~> 0.3.2"


Thanks for replying, Benny! 
>
> On 2019-10-6 11:06 PM, Benny Degezelle wrote: 
> > I've set up a 1.9.3-p551 with rubygems 1.8.29 on my machine (Ubuntu 
> > 18.04), bundle update does not give me that error. 
> > 
> > My next guess would be that there's an issue with your SSL... 
> > Have you tried changing https://rubygems.org to http://rubygems.org in 
> > the Gemfile? 
>
> That was it! That did work for me (switching to http). 
>
> However, I find that it fails a lot asking for newer Ruby :-( 
>
> So far, I have done special installs for rack-cache, rake, i18n, and now 
> it complains of zeitwerk that never seems to have worked with an older 
> Ruby. It seems to be pulled in by paper-clip and I still have to find a 
> version of paper-clip that works. 
>
> I do have an old site for which I have the Gemfile.lock, and maybe, I 
> should go through that, installing each gem one by one as per the 
> versions there (that was with Radiant 0.7.0) but at least it used to work. 
>
> Best Regards, 
> Mohit. 
> 2019-10-7 | 9:11 PM. 
>
>

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