Sometimes I randomly have the same problem that Garmin Express does not acknowledge the entitlement to a map update for a Lifetime Mapupdate device I have. I then use Garmin MapUpdater instead.
If that application also denies access to a map update, contact Garmin about the issue. Please note that (officially) the entitlement to Lifetime Mapupdates for a particular device expires two years after the last time a Lifetime Mapupdate was installed on that device. If you contact Garmin, don't do it by email or contact form. Use the phone. First of all, Garmin is not exactly known for its prompt response to email. Secondly, when talking live to a Customer Service Agent, they may be more inclined to accomodate you then when using a rather impersonal email service.
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