Thrain and 🧙Gandalf in Dol Guldur

[Ithrynluin]

It is said in Unfinished Tales; The Quest of Erebor:

It was nine years after Thrain had left his people that I found him, and he had then been in the pits of Dol Guldur for five years at least. I do not know how he endured so long, nor how he had kept these things hidden through all his torments.

How did Thrain manage to keep the map and the key to Erebor hidden from Sauron?

Later on, this is explained, to an extent:

I think that the Dark Power had desired nothing from him except the Ring only, and when he had taken that he troubled no further, but just flung the broken prisoner into the pits to rave until he died. A small oversight; but it proved fatal. Small oversights often do."

Why did Sauron let this happen? Isn't it better to strip your enemy of anything important, even if it doesn't hold much value to you or even if there is no chance for his escape?
Was Sauron simply being over-confident and full of hubris?

Another related question would be, how did Gandalf manage to enter Dol Guldur? It is said he had a disguise, what could that have been? Orc garments similar to those that Frodo and Sam wore in Morodor? I find it rather unbelievable that Gandalf went unnoticed and didn't get questioned at least upon entering the dungeons where Thrain lay. Or was this over-confidence on Sauron's part as well, thinking that Gandalf couldn't discover anything of value here, and having in mind that he would flee soon to Mordor? Was Sauron aware of Gandalf's presence?

From The Return of the King; The Black Gate Opens
‘So!’ said the Messenger. ‘Then thou art the spokesman, old greybeard? Have we not heard of thee at whiles, and of thy wanderings, ever hatching plots and mischief at a safe distance? But this time thou hast stuck out thy nose too far, Master Gandalf; and thou shalt see what comes to him who sets his foolish webs before the feet of Sauron the Great. I have tokens that I was bidden to show to thee - to thee in especial, if thou shouldst dare to come.’ He signed to one of his guards, and he came forward bearing a bundle swathed in black cloths.

This seems to indicate that they were aware of many of Gandalf's movements, but it is uncertain...

 

[Beleg]

This seems to indicate that they were aware of many of Gandalf's movements, but it is uncertain...

Have we not heard of thee at whiles, and of thy wanderings, ever hatching plots and mischief at a safe distance?

But IF Sauron was aware of Gandalf's presence in Dol-Guldor then why did the Mouth of Sauron said the phrase "safe distance."? Yes probably it is uncertain...

Another related question would be, how did Gandalf manage to enter Dol Guldur? It is said he had a disguise, what could that have been? Orc garments similar to those that Frodo and Sam wore in Morodor?

Reminds me of Felagund and Saurons encounter.

Why did Sauron let this happen? Isn't it better to strip your enemy of anything important, even if it doesn't hold much value to you or even if there is no chance for his escape?

Perhaps Sauron was wholly engrossed in the lust and finding of the ring and so wouldn't have cared a great deal even if he had found the key and the map? Or perhaps he discovered the ring first and was overjoyed with its finding that he paid no more heed towards Thrain and his other possessions.

Isn't it better to strip your enemy of anything important, even if it doesn't hold much value to you or even if there is no chance for his escape?

It is, but when you suddenly find some great joy or hear a happy news, you tend to forget the other, more minor things that are happening around you.

 

[Thorondor_]

Another related question would be, how did Gandalf manage to enter Dol Guldur?

If I remember correctly, the valar were rather invisible to commoners, and they could show themselves if they wanted to. Gandalf is a maia, so he must have inherited some "disguising" traits also.

 

[Arthur_Vandelay]

Was Sauron in Dol Guldur as powerful as he would be later in Mordor (c. The War of the Ring)?

 

[Thorondor_]

For it is said indeed that being embodied the Istari had needs to learn much anew by slow experience

So my answer to your question would be no.

 

[Inderjit S]

Was Sauron in Dol Guldur as powerful as he would be later in Mordor (c. The War of the Ring)?

Yes-I doubt Sauron's inherent power increased a lot over a few decades.

 

[Arthur_Vandelay]

Yes-I doubt Sauron's inherent power increased a lot over a few decades.

Okay--but perhaps in Dol Guldur he had less formidable forces at his disposal. Perhaps Dol Guldur was guarded less vigilantly than the gates of Mordor. Perhaps Gandalf had at his disposal some means of disguising his power, as Thorondor_ suggests. It does seem unusual that Sauron would not have detected his presence.

 

[Thorondor_]

Isn't it said all over the LotR that the Shadow is growing? I doubt it reffers only to the number of soldiers, I believe it reffers also to Sauron's power.