Alexandre Silva Those file sizes are absolutely the root cause of your ongoing indexing loop. You are dealing with roughly ninety gigabytes of mail data, and because you are running the 32-bit version of Office, the search protocol handler is restricted to a strict two-gigabyte memory limit. When Windows Search attempts to scan and map that massive volume of information, the 32-bit background process completely exhausts its available memory, crashes, and forces the indexer to restart from the beginning. Disabling the Windows service works temporarily because it forces Outlook to bypass the operating system and rely on its own slower, built-in query mechanism, but it does not solve the underlying architectural bottleneck.
To resolve this issue while keeping Windows Search fully enabled, the most effective solution is to uninstall your 32-bit Office suite and install the 64-bit version. The 64-bit architecture removes this memory ceiling, allowing the search handler to easily process massive data files without crashing. If migrating to 64-bit Office is not an option for you right now, you must significantly reduce the amount of data the indexer is forced to read. You can accomplish this by opening your Outlook Account Settings, double-clicking your email accounts, and adjusting the offline cache slider down to six months or one year. This will force Outlook to shrink those massive data files to a manageable size that your 32-bit indexer can process without running out of memory.
Hope this helps :)
VP