Apply for family permit while residence card app pending?

I am Italian, married with a Bolivian. We live in UK.
His UK Visa expired a few months ago, he overstayed in UK.
My husband applied for a residence card that will be issued by May 2016.
He recently received the Certificate of Application stating that he can work in UK whilst the application is processed.
We would like to go to Italy for Christmas.
I spoke with the Italian Embassy and they told me that my husband will be given a Shengen visa and there are no problems for him to travel to Italy with me.
The problems is how he can re-enter to UK.

According to my lawyer
1)In theory he has the right to be re-enter to UK, as according to EU he doesn't need a residence card to be in UK as he is family member of me (I live and work in UK since the past 8+ years) but "on the ground" the situation might be different and he might be refused to enter as our marriage (celebrated in London and registered in Italy) has not been acknowledged yet by the Home Office (!?) and because of his poor immigration history.
My lawyer also told me that carriers may refuse to board him without a visa. He doesn't need a visa! Do you know what's Ryanair policy?

I asked the lawyer if he can apply for a family permit while we are in Italy but she said he has to go back to Bolivia to apply for it (?!) There is no mention of this on the website https://www.gov.uk/family-permit/overview
It looks he only needs to be abroad.

Can any of you advise?

Can my husband apply for UK Family permit in Italy whist his residence card application is pending?

I simply want to spend Christmas with my family.

italianwife wrote:I am Italian, married with a Bolivian. We live in UK.
His UK Visa expired a few months ago, he overstayed in UK.
My husband applied for a residence card that will be issued by May 2016.
He recently received the Certificate of Application stating that he can work in UK whilst the application is processed.
We would like to go to Italy for Christmas.
...
The problems is how he can re-enter to UK.

According to my lawyer
1)In theory he has the right to be re-enter to UK, as according to EU he doesn't need a residence card to be in UK as he is family member of me (I live and work in UK since the past 8+ years) but "on the ground" the situation might be different and he might be refused to enter as our marriage (celebrated in London and registered in Italy) has not been acknowledged yet by the Home Office (!?) and because of his poor immigration history.
My lawyer also told me that carriers may refuse to board him without a visa. He doesn't need a visa! Do you know what's Ryanair policy?

...

I simply want to spend Christmas with my family.

This thread topic may help with reentry - option 2 appears to apply in your case:
http://www.immigrationboards.com/europe ... 95372.html

>>Article 5, Section 4 of 2004/38/EC << reads as follows:

Where a Union citizen, or a family member who is not a national of a Member State, does not have the necessary travel documents or, if required, the necessary visas, the Member State concerned shall, before turning them back, give such persons every reasonable opportunity to obtain the necessary documents or have them brought to them within a reasonable period of time or to corroborate or prove by other means that they are covered by the right of free movement and residence.

fyi - see following Border Force operations manuals for insight on how your reentry to UK may be handled:
https://www.whatdotheyknow.com/request/ ... ndents.pdf
- for example, see section 5 and section 5.5 in particular

See also https://www.whatdotheyknow.com/request/ ... ionals.pdf

Bon voyage & happy holiday!

Similar travel question here:
http://www.immigrationboards.com/eea-ro ... l#p1178943