That's a fun read.

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'But very bright were the stars upon the margin of the world, when at times the clouds about the West were drawn aside.'

It is an interesting question that hasn't been discussed much - what was Gandalf's plan? He reacts with distress to the news that Gollum has taken the hobbits up Cirith Ungol, he must have known the Black Gate was impassable, and I can't see how he would have taken the Morgul Pass either. How did he intend to get the Fellowship into Mordor?

I think Gandalf's plan was to play it by ear, and trust that Eru would find a way.

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'But very bright were the stars upon the margin of the world, when at times the clouds about the West were drawn aside.'

Bit of a crap plan really.

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The Vinyamars on Stage! This time at Bag End

IAWA
Although I think it more likely that he started out with the knowledge that no plan survives contact with the enemy and that he had with him four experienced campaigners. He more likely planned to reach Lórien, gather intel and consult with Galadriel before deciding how to proceed.

Also, to LM's point, perhaps Cirith Ungol was an option. With Aragorn, Legolas and Gimli (assuming Boromir survived but took off for Minas Tirith), Gandalf could reasonably hope to at least distract Shelob enough to get the hobbits through.

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“It may help to understand human affairs to be clear that most of the great triumphs and tragedies of history are caused, not by people being fundamentally good or fundamentally bad, but by people being fundamentally people.”

- Terry Pratchett & Neil Gaiman, Good Omens

On the other hand, after rejoining them, he was pleased to hear that Sam had joined Frodo, and then was dismayed to hear about Cirith Ungol. Which implies that there was an alternate route that he was hoping they would take.

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Maybe he thought hobbit stealth would allow Frodo to sneak through the Gate?

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“It may help to understand human affairs to be clear that most of the great triumphs and tragedies of history are caused, not by people being fundamentally good or fundamentally bad, but by people being fundamentally people.”

- Terry Pratchett & Neil Gaiman, Good Omens

Or continue East past the Morannon and come in via Nurn while everyone else was going out the front gate?

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The Vinyamars on Stage! This time at Bag End

So nobody buys the explanation I posted?

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I wanna love somebody but I don't know how
I wanna throw my body in the river and drown
-The Decemberists

Oh, it's possible - we're just speculating about his Plan B.

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