diff --git a/platform-darwin/Source/MPConfig.h b/platform-darwin/Source/MPConfig.h
index 844e993a..f40da91e 100644
--- a/platform-darwin/Source/MPConfig.h
+++ b/platform-darwin/Source/MPConfig.h
@@ -21,6 +21,7 @@
 @interface MPConfig : PearlConfig
 
 @property(nonatomic, retain) NSNumber *sendInfo;
+@property(nonatomic, retain) NSNumber *sendInfoDecided;
 @property(nonatomic, retain) NSNumber *rememberLogin;
 @property(nonatomic, retain) NSNumber *hidePasswords;
 
diff --git a/platform-darwin/Source/MPConfig.m b/platform-darwin/Source/MPConfig.m
index 0168abb3..24381e42 100644
--- a/platform-darwin/Source/MPConfig.m
+++ b/platform-darwin/Source/MPConfig.m
@@ -29,13 +29,15 @@
         return nil;
 
     [self.defaults registerDefaults:@{
-            NSStringFromSelector( @selector( askForReviews ) )     : @YES,
-
             NSStringFromSelector( @selector( sendInfo ) )          : @YES,
+            NSStringFromSelector( @selector( sendInfoDecided ) )   : @NO,
+
             NSStringFromSelector( @selector( rememberLogin ) )     : @NO,
             NSStringFromSelector( @selector( hidePasswords ) )     : @NO,
-            NSStringFromSelector( @selector( checkInconsistency ) ): @NO,
             NSStringFromSelector( @selector( siteAttacker ) )      : @(MPAttacker1),
+
+            NSStringFromSelector( @selector( checkInconsistency ) ): @NO,
+            NSStringFromSelector( @selector( askForReviews ) )     : @YES,
     }];
 
     self.delegate = [MPAppDelegate_Shared get];
diff --git a/platform-darwin/Source/Mac/MPMacAppDelegate.m b/platform-darwin/Source/Mac/MPMacAppDelegate.m
index 0f2251c5..664bffd3 100644
--- a/platform-darwin/Source/Mac/MPMacAppDelegate.m
+++ b/platform-darwin/Source/Mac/MPMacAppDelegate.m
@@ -86,7 +86,7 @@ static OSStatus MPHotKeyHander(EventHandlerCallRef nextHandler, EventRef theEven
         }];
         [[PearlLogger get] registerListener:^BOOL(PearlLogMessage *message) {
             PearlLogLevel level = PearlLogLevelWarn;
-            if ([[MPConfig get].sendInfo boolValue])
+            if ([[MPMacConfig get].sendInfo boolValue])
                 level = PearlLogLevelDebug;
 
             if (message.level >= level) {
@@ -145,7 +145,7 @@ static OSStatus MPHotKeyHander(EventHandlerCallRef nextHandler, EventRef theEven
     }
 
     // Setup delegates and listeners.
-    [MPConfig get].delegate = self;
+    [MPMacConfig get].delegate = self;
     __weak id weakSelf = self;
     [self addObserverBlock:^(NSString *keyPath, id object, NSDictionary *change, void *context) {
         dispatch_async( dispatch_get_main_queue(), ^{
@@ -210,7 +210,7 @@ static OSStatus MPHotKeyHander(EventHandlerCallRef nextHandler, EventRef theEven
 
 - (void)applicationWillResignActive:(NSNotification *)notification {
 
-    if (![[MPConfig get].rememberLogin boolValue])
+    if (![[MPMacConfig get].rememberLogin boolValue])
         [self lock:nil];
 }
 
@@ -408,12 +408,18 @@ static OSStatus MPHotKeyHander(EventHandlerCallRef nextHandler, EventRef theEven
 
 - (IBAction)togglePreference:(id)sender {
 
-    if (sender == self.diagnosticsItem)
-        [MPConfig get].sendInfo = @(self.diagnosticsItem.state != NSOnState);
+    if (sender == self.diagnosticsItem) {
+        BOOL sendInfo = self.diagnosticsItem.state != NSOnState;
+        [[Countly sharedInstance] recordEvent:@"sendInfoDecided" segmentation:@{
+                @"from": @"preferences",
+                @"sendInfo": [@(sendInfo) description],
+            }];
+        [MPMacConfig get].sendInfo = @(sendInfo);
+    }
     if (sender == self.hidePasswordsItem)
-        [MPConfig get].hidePasswords = @(self.hidePasswordsItem.state != NSOnState);
+        [MPMacConfig get].hidePasswords = @(self.hidePasswordsItem.state != NSOnState);
     if (sender == self.rememberPasswordItem)
-        [MPConfig get].rememberLogin = @(self.rememberPasswordItem.state != NSOnState);
+        [MPMacConfig get].rememberLogin = @(self.rememberPasswordItem.state != NSOnState);
     if (sender == self.openAtLoginItem)
         [self setLoginItemEnabled:self.openAtLoginItem.state != NSOnState];
     if (sender == self.showFullScreenItem) {
@@ -760,26 +766,26 @@ static OSStatus MPHotKeyHander(EventHandlerCallRef nextHandler, EventRef theEven
 
     PearlMainQueue( ^{
         if (!key || [key isEqualToString:NSStringFromSelector( @selector( sendInfo ) )])
-            self.diagnosticsItem.state = [[MPConfig get].sendInfo boolValue]? NSOnState: NSOffState;
+            self.diagnosticsItem.state = [[MPMacConfig get].sendInfo boolValue]? NSOnState: NSOffState;
         if (!key || [key isEqualToString:NSStringFromSelector( @selector( hidePasswords ) )])
-            self.hidePasswordsItem.state = [[MPConfig get].hidePasswords boolValue]? NSOnState: NSOffState;
+            self.hidePasswordsItem.state = [[MPMacConfig get].hidePasswords boolValue]? NSOnState: NSOffState;
         if (!key || [key isEqualToString:NSStringFromSelector( @selector( rememberLogin ) )])
-            self.rememberPasswordItem.state = [[MPConfig get].rememberLogin boolValue]? NSOnState: NSOffState;
+            self.rememberPasswordItem.state = [[MPMacConfig get].rememberLogin boolValue]? NSOnState: NSOffState;
     } );
 
     // Send info
     NSArray *countlyFeatures = @[
             CLYConsentSessions, CLYConsentEvents, CLYConsentUserDetails, CLYConsentCrashReporting, CLYConsentViewTracking, CLYConsentStarRating
     ];
-    if ([[MPConfig get].sendInfo boolValue]) {
+    if ([[MPMacConfig get].sendInfo boolValue]) {
         [Countly.sharedInstance giveConsentForFeatures:countlyFeatures];
         if ([PearlLogger get].printLevel > PearlLogLevelInfo)
             [PearlLogger get].printLevel = PearlLogLevelInfo;
 
         [SentrySDK.currentHub getClient].options.enabled = @YES;
         [SentrySDK configureScope:^(SentryScope *scope) {
-            [scope setExtraValue:[MPConfig get].rememberLogin forKey:@"rememberLogin"];
-            [scope setExtraValue:[MPConfig get].sendInfo forKey:@"sendInfo"];
+            [scope setExtraValue:[MPMacConfig get].rememberLogin forKey:@"rememberLogin"];
+            [scope setExtraValue:[MPMacConfig get].sendInfo forKey:@"sendInfo"];
             [scope setExtraValue:[MPMacConfig get].fullScreen forKey:@"fullScreen"];
             [scope setExtraValue:[PearlConfig get].firstRun forKey:@"firstRun"];
             [scope setExtraValue:[PearlConfig get].launchCount forKey:@"launchCount"];
diff --git a/platform-darwin/Source/Mac/MPSitesWindowController.m b/platform-darwin/Source/Mac/MPSitesWindowController.m
index d4fb7857..abfa591d 100644
--- a/platform-darwin/Source/Mac/MPSitesWindowController.m
+++ b/platform-darwin/Source/Mac/MPSitesWindowController.m
@@ -17,6 +17,7 @@
 //==============================================================================
 
 #import <QuartzCore/QuartzCore.h>
+#import <Countly/Countly.h>
 #import "MPSitesWindowController.h"
 #import "MPMacAppDelegate.h"
 #import "MPAppDelegate_Store.h"
@@ -42,13 +43,35 @@
     prof_rewind( @"replaceFonts" );
 
     PearlAddNotificationObserver( NSWindowDidBecomeKeyNotification, self.window, [NSOperationQueue mainQueue],
-            ^(id host, NSNotification *note) {
+            (^(id host, NSNotification *note) {
                 prof_new( @"didBecomeKey" );
                 [self.window makeKeyAndOrderFront:nil];
                 prof_rewind( @"fadeIn" );
                 [self updateUser];
-                prof_finish( @"updateUser" );
-            } );
+                prof_rewind( @"updateUser" );
+
+                if (![[MPMacConfig get].sendInfoDecided boolValue]) {
+                    NSAlert *alert = [NSAlert new];
+                    alert.messageText = @"Welcome to Master Password!";
+                    alert.informativeText = @"We want you to have a top-notch experience.\n"
+                                            @"Using diagnostics, we ensure the application keeps working as designed for you.\n"
+                                            @"\n"
+                                            @"We look out for application bugs, runtime issues, sudden crashes & usage counters.\n"
+                                            @"Needless to say, diagnostics are always scrubbed and personal details will never leave your device.";
+                    [alert addButtonWithTitle:@"Thanks!"];
+                    [alert addButtonWithTitle:@"Disable"];
+                    [alert beginSheetModalForWindow:self.window completionHandler:^(NSModalResponse returnCode) {
+                        BOOL sendInfo = returnCode != NSAlertSecondButtonReturn;
+                        [[Countly sharedInstance] recordEvent:@"sendInfoDecided" segmentation:@{
+                                @"from": @"initial",
+                                @"sendInfo": [@(sendInfo) description],
+                        }];
+                        [MPMacConfig get].sendInfo = @(sendInfo);
+                        [MPMacConfig get].sendInfoDecided = @(YES);
+                    }];
+                }
+                prof_finish( @"sendInfoDecided" );
+            }) );
     PearlAddNotificationObserver( NSWindowWillCloseNotification, self.window, [NSOperationQueue mainQueue],
             ^(id host, NSNotification *note) {
                 NSWindow *sheet = [self.window attachedSheet];