Let's Encrypt fails when requesting SSL certificate

Getting this error when attenotubg to issue an SSL cert w/ Lets Encrypt via Virtualmin:

Validating configuration for herohousecreative.com .. .. no problems found Requesting a certificate for herohousecreative.com, www.herohousecreative.com, autoconfig.herohousecreative.com, autodiscover.herohousecreative.com from Let's Encrypt .. .. request failed : Web-based validation failed : Bootstrapping dependencies for Debian-based OSes... (you can skip this with --no-bootstrap) Ign http://mirrors.digitalocean.com trusty InRelease Hit http://mirrors.digitalocean.com trusty-updates InRelease Ign http://software.virtualmin.com virtualmin-trusty InRelease Hit http://mirrors.digitalocean.com trusty-backports InRelease Hit http://mirrors.digitalocean.com trusty Release.gpg Ign http://software.virtualmin.com virtualmin-universal InRelease Hit http://mirrors.digitalocean.com trusty-updates/main Sources Hit http://mirrors.digitalocean.com trusty-updates/restricted Sources Hit http://software.virtualmin.com virtualmin-trusty Release.gpg Hit http://mirrors.digitalocean.com trusty-updates/universe Sources Hit http://mirrors.digitalocean.com trusty-updates/multiverse Sources Hit http://software.virtualmin.com virtualmin-universal Release.gpg Hit http://mirrors.digitalocean.com trusty-updates/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-updates/restricted amd64 Packages Hit http://software.virtualmin.com virtualmin-trusty Release Hit http://mirrors.digitalocean.com trusty-updates/universe amd64 Packages Hit http://mirrors.digitalocean.com trusty-updates/multiverse amd64 Packages Hit http://mirrors.digitalocean.com trusty-updates/main i386 Packages Hit http://software.virtualmin.com virtualmin-universal Release Hit http://mirrors.digitalocean.com trusty-updates/restricted i386 Packages Hit http://ppa.launchpad.net trusty InRelease Hit http://mirrors.digitalocean.com trusty-updates/universe i386 Packages Hit http://software.virtualmin.com virtualmin-trusty/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-updates/multiverse i386 Packages Hit http://software.virtualmin.com virtualmin-trusty/main i386 Packages Hit http://mirrors.digitalocean.com trusty-updates/main Translation-en Hit http://mirrors.digitalocean.com trusty-updates/multiverse Translation-en Hit http://mirrors.digitalocean.com trusty-updates/restricted Translation-en Hit http://mirrors.digitalocean.com trusty-updates/universe Translation-en Ign http://archive.ubuntu.com trusty InRelease Hit http://security.ubuntu.com trusty-security InRelease Hit http://mirrors.digitalocean.com trusty-backports/main Sources Hit http://mirrors.digitalocean.com trusty-backports/restricted Sources Hit http://software.virtualmin.com virtualmin-universal/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-backports/universe Sources Hit http://mirrors.digitalocean.com trusty-backports/multiverse Sources Hit http://software.virtualmin.com virtualmin-universal/main i386 Packages Hit http://mirrors.digitalocean.com trusty-backports/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-backports/restricted amd64 Packages Hit http://mirrors.digitalocean.com trusty-backports/universe amd64 Packages Hit http://archive.ubuntu.com trusty Release.gpg Hit http://mirrors.digitalocean.com trusty-backports/multiverse amd64 Packages Hit http://ppa.launchpad.net trusty InRelease Hit http://mirrors.digitalocean.com trusty-backports/main i386 Packages Hit http://security.ubuntu.com trusty-security/main Sources Hit http://mirrors.digitalocean.com trusty-backports/restricted i386 Packages Hit http://mirrors.digitalocean.com trusty-backports/universe i386 Packages Hit http://mirrors.digitalocean.com trusty-backports/multiverse i386 Packages Hit http://mirrors.digitalocean.com trusty-backports/main Translation-en Hit http://mirrors.digitalocean.com trusty-backports/multiverse Translation-en Hit http://archive.ubuntu.com trusty Release Hit http://security.ubuntu.com trusty-security/universe Sources Hit http://mirrors.digitalocean.com trusty-backports/restricted Translation-en Hit http://mirrors.digitalocean.com trusty-backports/universe Translation-en Hit http://mirrors.digitalocean.com trusty Release Hit http://mirrors.digitalocean.com trusty/main Sources Hit http://mirrors.digitalocean.com trusty/restricted Sources Hit http://archive.ubuntu.com trusty/universe amd64 Packages Hit http://ppa.launchpad.net trusty/main amd64 Packages Hit http://mirrors.digitalocean.com trusty/universe Sources Hit http://security.ubuntu.com trusty-security/main amd64 Packages Hit http://mirrors.digitalocean.com trusty/multiverse Sources Hit http://mirrors.digitalocean.com trusty/main amd64 Packages Ign http://software.virtualmin.com virtualmin-trusty/main Translation-en Hit http://mirrors.digitalocean.com trusty/restricted amd64 Packages Ign http://software.virtualmin.com virtualmin-universal/main Translation-en Hit http://mirrors.digitalocean.com trusty/universe amd64 Packages Hit http://archive.ubuntu.com trusty/universe i386 Packages Hit http://mirrors.digitalocean.com trusty/multiverse amd64 Packages Hit http://mirrors.digitalocean.com trusty/main i386 Packages Hit http://security.ubuntu.com trusty-security/universe amd64 Packages Hit http://mirrors.digitalocean.com trusty/restricted i386 Packages Hit http://mirrors.digitalocean.com trusty/universe i386 Packages Hit http://mirrors.digitalocean.com trusty/multiverse i386 Packages Hit http://mirrors.digitalocean.com trusty/main Translation-en Hit http://mirrors.digitalocean.com trusty/multiverse Translation-en Hit http://mirrors.digitalocean.com trusty/restricted Translation-en Hit http://archive.ubuntu.com trusty/universe Translation-en Hit http://security.ubuntu.com trusty-security/main i386 Packages Hit http://ppa.launchpad.net trusty/main i386 Packages Hit https://esm.ubuntu.com trusty-infra-security InRelease Hit http://mirrors.digitalocean.com trusty/universe Translation-en Hit http://security.ubuntu.com trusty-security/universe i386 Packages Hit https://esm.ubuntu.com trusty-infra-updates InRelease Hit http://security.ubuntu.com trusty-security/main Translation-en Hit http://ppa.launchpad.net trusty/main Translation-en Hit https://esm.ubuntu.com trusty-infra-security/main amd64 Packages Hit http://security.ubuntu.com trusty-security/universe Translation-en Hit https://esm.ubuntu.com trusty-infra-security/main i386 Packages Hit http://ppa.launchpad.net trusty/main amd64 Packages Get:1 https://esm.ubuntu.com trusty-infra-security/main Translation-en Hit https://esm.ubuntu.com trusty-infra-updates/main amd64 Packages Hit http://ppa.launchpad.net trusty/main i386 Packages Hit https://esm.ubuntu.com trusty-infra-updates/main i386 Packages Get:2 https://esm.ubuntu.com trusty-infra-updates/main Translation-en Hit http://ppa.launchpad.net trusty/main Translation-en Ign https://esm.ubuntu.com trusty-infra-security/main Translation-en Ign https://esm.ubuntu.com trusty-infra-updates/main Translation-en Reading package lists... Reading package lists... Building dependency tree... Reading state information... gcc is already the newest version. gcc set to manually installed. python is already the newest version. ca-certificates is already the newest version. openssl is already the newest version. Some packages could not be installed. This may mean that you have requested an impossible situation or if you are using the unstable distribution that some required packages have not yet been created or been moved out of Incoming. The following information may help to resolve the situation:

The following packages have unmet dependencies: libssl-dev : Depends: libssl1.0.0 (= 1.0.1f-1ubuntu2.27) but 1.0.2k-1+deb.sury.org~trusty+1 is to be installed E: Unable to correct problems, you have held broken packages. DNS-based validation failed : Bootstrapping dependencies for Debian-based OSes... (you can skip this with --no-bootstrap) Ign http://mirrors.digitalocean.com trusty InRelease Hit http://mirrors.digitalocean.com trusty-updates InRelease Hit http://mirrors.digitalocean.com trusty-backports InRelease Hit http://mirrors.digitalocean.com trusty Release.gpg Ign http://software.virtualmin.com virtualmin-trusty InRelease Hit http://mirrors.digitalocean.com trusty-updates/main Sources Hit http://mirrors.digitalocean.com trusty-updates/restricted Sources Ign http://software.virtualmin.com virtualmin-universal InRelease Hit http://security.ubuntu.com trusty-security InRelease Hit http://mirrors.digitalocean.com trusty-updates/universe Sources Hit http://mirrors.digitalocean.com trusty-updates/multiverse Sources Hit http://software.virtualmin.com virtualmin-trusty Release.gpg Hit http://mirrors.digitalocean.com trusty-updates/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-updates/restricted amd64 Packages Hit http://software.virtualmin.com virtualmin-universal Release.gpg Hit http://mirrors.digitalocean.com trusty-updates/universe amd64 Packages Hit http://security.ubuntu.com trusty-security/main Sources Hit http://software.virtualmin.com virtualmin-trusty Release Hit http://mirrors.digitalocean.com trusty-updates/multiverse amd64 Packages Hit http://ppa.launchpad.net trusty InRelease Hit http://mirrors.digitalocean.com trusty-updates/main i386 Packages Ign http://archive.ubuntu.com trusty InRelease Hit http://mirrors.digitalocean.com trusty-updates/restricted i386 Packages Hit http://software.virtualmin.com virtualmin-universal Release Hit http://security.ubuntu.com trusty-security/universe Sources Hit http://mirrors.digitalocean.com trusty-updates/universe i386 Packages Hit http://software.virtualmin.com virtualmin-trusty/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-updates/multiverse i386 Packages Hit http://mirrors.digitalocean.com trusty-updates/main Translation-en Hit http://security.ubuntu.com trusty-security/main amd64 Packages Hit http://software.virtualmin.com virtualmin-trusty/main i386 Packages Hit http://archive.ubuntu.com trusty Release.gpg Hit http://security.ubuntu.com trusty-security/universe amd64 Packages Hit http://mirrors.digitalocean.com trusty-updates/multiverse Translation-en Hit http://software.virtualmin.com virtualmin-universal/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-updates/restricted Translation-en Hit http://software.virtualmin.com virtualmin-universal/main i386 Packages Hit http://mirrors.digitalocean.com trusty-updates/universe Translation-en Hit http://security.ubuntu.com trusty-security/main i386 Packages Hit http://mirrors.digitalocean.com trusty Release Hit http://ppa.launchpad.net trusty InRelease Hit https://esm.ubuntu.com trusty-infra-security InRelease Hit http://archive.ubuntu.com trusty Release Hit http://mirrors.digitalocean.com trusty-backports/main Sources Hit http://mirrors.digitalocean.com trusty-backports/restricted Sources Hit http://security.ubuntu.com trusty-security/universe i386 Packages Hit http://mirrors.digitalocean.com trusty-backports/universe Sources Hit https://esm.ubuntu.com trusty-infra-updates InRelease Hit http://mirrors.digitalocean.com trusty-backports/multiverse Sources Hit http://mirrors.digitalocean.com trusty-backports/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-backports/restricted amd64 Packages Hit http://security.ubuntu.com trusty-security/main Translation-en Hit http://mirrors.digitalocean.com trusty-backports/universe amd64 Packages Hit https://esm.ubuntu.com trusty-infra-security/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-backports/multiverse amd64 Packages Hit http://archive.ubuntu.com trusty/universe amd64 Packages Hit http://mirrors.digitalocean.com trusty-backports/main i386 Packages Hit http://security.ubuntu.com trusty-security/universe Translation-en Hit http://mirrors.digitalocean.com trusty-backports/restricted i386 Packages Hit https://esm.ubuntu.com trusty-infra-security/main i386 Packages Hit http://mirrors.digitalocean.com trusty-backports/universe i386 Packages Hit http://mirrors.digitalocean.com trusty-backports/multiverse i386 Packages Hit http://ppa.launchpad.net trusty/main amd64 Packages Hit http://mirrors.digitalocean.com trusty-backports/main Translation-en Get:1 https://esm.ubuntu.com trusty-infra-security/main Translation-en Hit http://mirrors.digitalocean.com trusty-backports/multiverse Translation-en Hit http://archive.ubuntu.com trusty/universe i386 Packages Hit http://mirrors.digitalocean.com trusty-backports/restricted Translation-en Hit http://mirrors.digitalocean.com trusty-backports/universe Translation-en Hit https://esm.ubuntu.com trusty-infra-updates/main amd64 Packages Hit http://mirrors.digitalocean.com trusty/main Sources Ign http://software.virtualmin.com virtualmin-trusty/main Translation-en Hit http://mirrors.digitalocean.com trusty/restricted Sources Hit http://mirrors.digitalocean.com trusty/universe Sources Hit http://mirrors.digitalocean.com trusty/multiverse Sources Ign http://software.virtualmin.com virtualmin-universal/main Translation-en Hit http://archive.ubuntu.com trusty/universe Translation-en Hit https://esm.ubuntu.com trusty-infra-updates/main i386 Packages Hit http://mirrors.digitalocean.com trusty/main amd64 Packages Hit http://mirrors.digitalocean.com trusty/restricted amd64 Packages Hit http://mirrors.digitalocean.com trusty/universe amd64 Packages Hit http://mirrors.digitalocean.com trusty/multiverse amd64 Packages Get:2 https://esm.ubuntu.com trusty-infra-updates/main Translation-en Hit http://mirrors.digitalocean.com trusty/main i386 Packages Hit http://mirrors.digitalocean.com trusty/restricted i386 Packages Hit http://ppa.launchpad.net trusty/main i386 Packages Hit http://mirrors.digitalocean.com trusty/universe i386 Packages Hit http://mirrors.digitalocean.com trusty/multiverse i386 Packages Hit http://mirrors.digitalocean.com trusty/main Translation-en Hit http://mirrors.digitalocean.com trusty/multiverse Translation-en Hit http://mirrors.digitalocean.com trusty/restricted Translation-en Hit http://mirrors.digitalocean.com trusty/universe Translation-en Hit http://ppa.launchpad.net trusty/main Translation-en Ign https://esm.ubuntu.com trusty-infra-security/main Translation-en Hit http://ppa.launchpad.net trusty/main amd64 Packages Ign https://esm.ubuntu.com trusty-infra-updates/main Translation-en Hit http://ppa.launchpad.net trusty/main i386 Packages Hit http://ppa.launchpad.net trusty/main Translation-en Reading package lists... Reading package lists... Building dependency tree... Reading state information... gcc is already the newest version. gcc set to manually installed. python is already the newest version. ca-certificates is already the newest version. openssl is already the newest version. Some packages could not be installed. This may mean that you have requested an impossible situation or if you are using the unstable distribution that some required packages have not yet been created or been moved out of Incoming. The following information may help to resolve the situation:

The following packages have unmet dependencies: libssl-dev : Depends: libssl1.0.0 (= 1.0.1f-1ubuntu2.27) but 1.0.2k-1+deb.sury.org~trusty+1 is to be installed E: Unable to correct problems, you have held broken packages. <-  Return to virtual server details