Many who say that Naruto wouldn't Jiraiya and the reason he only got as far as he did and that Pein said that if Jiraiya had more information then he would've lost to him, but if you go by official Pein said that he would probably have lost in chapter 383.

https://s1.mangabeast01.com/manga/Naruto/0383-013.png

Keyword: Probably, which means that it's possible that he would've lost to Jiraiya not most definitely and if Jiraiya really thought that then he would've
tried to look for Nagato rather than giving the information before he died.

Another argument that Naruto didn't surpass Jiraiya because Itachi because of the fact that Itachi told Kisame that they could've both died if they had fought, but Miguel Soriano makes a good point when he said that Itachi was undercover he said this and gave details about why Itachi would beat Jiraiya here.


However, to address the Intel part.

1. Everyone in Kohana had much more knowledge than Naruto did, but that didn't stop destroying Kohana or nearly killing Tsunade

2. Naruto didn't get the information before the battle. He got it when he was fighting them. This makes a difference because giving information, while paying attention to the fight can be distracting.

Another argument that they like to make is that Naruto had Summonings aiding him in battle as well. Allow me to address

1. Jiraiya also used Summonings when fighting Pein as did Pein both when he was fighting Jiraiya and when he was fighting Naruto and since people like to say Kurama isn't Naruto's power then the same applies to Pein, since the Rinnegan was put in him by Obito.

2. Naruto has a contract with the toads, so he has every right to use them.

I know that a lot of people will say that Pein wasn't 100% and was weakened when facing Naruto.

1. To start things off Pein wasn't there that much longer than Naruto was.

2. It was Danzo who delayed Naruto's arrival in chapter 421 because he had killed the messenger frog


https://s1.mangabeast01.com/manga/Naruto/0421-017.png

Naruto didn't have much time to prepare for Pein in the battle, so when they were fighting he wasn't 100% either.

Fukkasaku confirms in chapter 430 that Naruto did surpass Jiraiya


https://official-complete.granpulse.us/manga/Naruto/0430-019.png


Before getting pinned Naruto took out Tendo Pein twice in chapter 433

https://official-complete.granpulse.us/manga/Naruto/0433-017.png

https://official-complete.granpulse.us/manga/Naruto/0433-023.png


Hinata's interference came in chapter 437 as did Kurama showing up as well and even people who believe that Jiraiya would win agree that Naruto is better at using Sage Mode than Jiraiya, but it's for that exact reason on why Naruto would beat Jiraiya and as I showed Fukkasaku confirmed that he did surpass Jiraiya.

Naruto slammed 2 Summoning Jutsus and nearly took out 4 Peins in 1 shot without information or Summoning Jutsus.

Chapter 430 takes out 1 of the Peins without intel or Summonings

https://s1.mangabeast01.com/manga/Naruto/0431-006.png


https://s1.mangabeast01.com/manga/Naruto/0430-017.png


Next chapter throws away a Summoning Jutsu without Intel or Summonings

https://s1.mangabeast01.com/manga/Naruto/0431-005.png

Chapter after that nearly takes out 4/6 Peins in 1 shot without Intel or Summonings


All of this concludes that Naruto did surpass Jiraiya and would've beaten him if they had fought during this time period.