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I found this question/answer when I ran into the same problem. I made a smaller repro, starting from batter.cord's, above. Salesforce support have confirmed that it is a bug and will be fixed, but there is no ETA for the fix. It's not currently on Known Issues, but I'll update if they add it.

FYI, my repro follows. The insertContact() test passes, the insertContentVersion() test fails.

@IsTest
private class ContentVersionBugRepro {

    public class MyQueueable implements Queueable, Database.AllowsCallouts {
        public void execute(QueueableContext param1) {
            Http connection = new Http();
            HttpRequest request = new HttpRequest();
            request.setEndpoint(System.Url.getOrgDomainUrl().toExternalForm());
            connection.send(request);
        }
    }

    public class MyMock implements HttpCalloutMock {
        public HttpResponse respond(HttpRequest param1) {
            return new HttpResponse();
        }
    }

    @IsTest static void insertContact() {
        insert new Contact(LastName = 'Test');

        Test.setMock(HttpCalloutMock.class, new MyMock());
        Test.startTest();
        System.enqueueJob(new MyQueueable());
        Test.stopTest();
    }

    @IsTest static void insertContentVersion() {
        insert new ContentVersion(
                VersionData = Blob.valueOf('someData'),
                PathOnClient = 'someData.txt'
        );

        Test.setMock(HttpCalloutMock.class, new MyMock());
        Test.startTest();
        System.enqueueJob(new MyQueueable());
        Test.stopTest();
    }
}