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You can't upload zip or rar because you have not included those extensions in your attachment manager.

As for the jpeg, as ssslippy said, you also have some php limits you may need to modify. All these settings may also effect your uploading of attachments:
PHP Settings:
max_execution_time
memory_limit
post_max_size
upload_max_filesize
max_input_time

MySQL Settings:
max_allowed_packet
max_packet_size
wait_timeout

X vBulletin 3.8.12 by vBS Debug Information
Template Usage: (1)SHOWTHREAD_SHOWPOST (1)ad_footer_end (1)ad_footer_start (1)ad_header_end (1)ad_header_logo (1)ad_navbar_below (1)footer (1)gobutton (1)header (1)headinclude (6)option (1)post_thanks_box (1)post_thanks_button (1)post_thanks_javascript (1)post_thanks_navbar_search (1)post_thanks_postbit_info (1)postbit (1)postbit_onlinestatus (1)postbit_wrapper (1)spacer_close (1)spacer_open Phrase Groups Available: global postbit reputationlevel showthread	Included Files: ./showpost.php ./global.php ./includes/init.php ./includes/class_core.php ./includes/config.php ./includes/functions.php ./includes/class_hook.php ./includes/modsystem_functions.php ./includes/functions_bigthree.php ./includes/class_postbit.php ./includes/class_bbcode.php ./includes/functions_reputation.php ./includes/functions_post_thanks.php Hooks Called: init_startup init_startup_session_setup_start init_startup_session_setup_complete cache_permissions fetch_postinfo_query fetch_postinfo fetch_threadinfo_query fetch_threadinfo fetch_foruminfo style_fetch cache_templates global_start parse_templates global_setup_complete showpost_start bbcode_fetch_tags bbcode_create postbit_factory showpost_post postbit_display_start post_thanks_function_post_thanks_off_start post_thanks_function_post_thanks_off_end post_thanks_function_fetch_thanks_start post_thanks_function_fetch_thanks_end post_thanks_function_thanked_already_start post_thanks_function_thanked_already_end fetch_musername postbit_imicons bbcode_parse_start bbcode_parse_complete_precache bbcode_parse_complete postbit_display_complete post_thanks_function_can_thank_this_post_start showpost_complete
Messages:

X vBulletin 3.8.12 by vBS Debug Information

Page Generation 0.01196 seconds
Memory Usage 1,757KB
Queries Executed 11 (?)

More Information

Template Usage:

(1)SHOWTHREAD_SHOWPOST
(1)ad_footer_end
(1)ad_footer_start
(1)ad_header_end
(1)ad_header_logo
(1)ad_navbar_below
(1)footer
(1)gobutton
(1)header
(1)headinclude
(6)option
(1)post_thanks_box
(1)post_thanks_button
(1)post_thanks_javascript
(1)post_thanks_navbar_search
(1)post_thanks_postbit_info
(1)postbit
(1)postbit_onlinestatus
(1)postbit_wrapper
(1)spacer_close
(1)spacer_open

Phrase Groups Available:

global
postbit
reputationlevel
showthread

Included Files:

./showpost.php
./global.php
./includes/init.php
./includes/class_core.php
./includes/config.php
./includes/functions.php
./includes/class_hook.php
./includes/modsystem_functions.php
./includes/functions_bigthree.php
./includes/class_postbit.php
./includes/class_bbcode.php
./includes/functions_reputation.php
./includes/functions_post_thanks.php

Hooks Called:

init_startup
init_startup_session_setup_start
init_startup_session_setup_complete
cache_permissions
fetch_postinfo_query
fetch_postinfo
fetch_threadinfo_query
fetch_threadinfo
fetch_foruminfo
style_fetch
cache_templates
global_start
parse_templates
global_setup_complete
showpost_start
bbcode_fetch_tags
bbcode_create
postbit_factory
showpost_post
postbit_display_start
post_thanks_function_post_thanks_off_start
post_thanks_function_post_thanks_off_end
post_thanks_function_fetch_thanks_start
post_thanks_function_fetch_thanks_end
post_thanks_function_thanked_already_start
post_thanks_function_thanked_already_end
fetch_musername
postbit_imicons
bbcode_parse_start
bbcode_parse_complete_precache
bbcode_parse_complete
postbit_display_complete
post_thanks_function_can_thank_this_post_start
showpost_complete

Messages:

X vBulletin 3.8.12 by vBS Debug Information
Page Generation 0.01196 seconds Memory Usage 1,757KB Queries Executed 11 (?)
More Information
Template Usage: (1)SHOWTHREAD_SHOWPOST (1)ad_footer_end (1)ad_footer_start (1)ad_header_end (1)ad_header_logo (1)ad_navbar_below (1)footer (1)gobutton (1)header (1)headinclude (6)option (1)post_thanks_box (1)post_thanks_button (1)post_thanks_javascript (1)post_thanks_navbar_search (1)post_thanks_postbit_info (1)postbit (1)postbit_onlinestatus (1)postbit_wrapper (1)spacer_close (1)spacer_open Phrase Groups Available: global postbit reputationlevel showthread	Included Files: ./showpost.php ./global.php ./includes/init.php ./includes/class_core.php ./includes/config.php ./includes/functions.php ./includes/class_hook.php ./includes/modsystem_functions.php ./includes/functions_bigthree.php ./includes/class_postbit.php ./includes/class_bbcode.php ./includes/functions_reputation.php ./includes/functions_post_thanks.php Hooks Called: init_startup init_startup_session_setup_start init_startup_session_setup_complete cache_permissions fetch_postinfo_query fetch_postinfo fetch_threadinfo_query fetch_threadinfo fetch_foruminfo style_fetch cache_templates global_start parse_templates global_setup_complete showpost_start bbcode_fetch_tags bbcode_create postbit_factory showpost_post postbit_display_start post_thanks_function_post_thanks_off_start post_thanks_function_post_thanks_off_end post_thanks_function_fetch_thanks_start post_thanks_function_fetch_thanks_end post_thanks_function_thanked_already_start post_thanks_function_thanked_already_end fetch_musername postbit_imicons bbcode_parse_start bbcode_parse_complete_precache bbcode_parse_complete postbit_display_complete post_thanks_function_can_thank_this_post_start showpost_complete
Messages: