The guards like her already, and Luthien's attention here deepens their friendship. They're supportive of Luthien's relationship, especially once they've solicited a few stories about Beren - especially the younger ones, the impatient ones, who want to take the fight to Morgoth.

And after a time - long enough for Beren to have reached Sauron's tower - Luthien gets a whisper in her mind,

'Now's a good time, darling. Your mother should see that I'm in trouble if she looks afar, though I don't think you need to be imprisoned first for this to work.'

Luthien spends two days quietly accumulating the last supplies she needs.

She heads out the gates while Thorndess is on duty.

"Have a good trip, my Lady," Thorndess says, voice soft and serious.

"Thank you."

And she's off.

The walk to Sauron's tower is long - longer, if she intends to go by Nargothrond first.

Still, nothing hinders her in leaving Doriath.

She already knows where to go, so she doesn't see the need to detour to Nargothrond. Direct to the tower it is.

It's almost like Mygwainor suspected she'd do that and made sure the right pieces were in place for the timeline's stability.

A certain excellent dog is waiting along the most obvious road.

"Hello, Huan."

Woof!

"Are you here to travel with me?"

Agreeable woof.

Smile.

"Well. Let's go, then."

They wag their tail and fall in beside Luthien, leading the way a little bit.

A bit of company is nice for the road. Especially some that won't ask too many questions.

Huan seems to appreciate this, too.

They draw near Sauron's Isle of Werewolves soon enough. Huan slinks along on their belly as they approach, ears and gaze intent. 

"Hear anything?" she asks quietly.

Grrr...

There's movement from the Isle - shapes emerging, slinking along. Werewolves, it looks like, stalking the perimeter.

"Need any help with them?"

They woof, shaking their head and wagging their tail a bit.

"All right. I'll head straight for the tower then, if you can keep them distracted."

Woof!

They dart forward through the grass, low to the ground and moving quickly. 

And Luthien moves for the tower, humming a song of stealth.

Huan pounces on a werewolf and procedes to steadily kick all their asses!

Then she just has to figure out how to get inside the tower.