diff --git a/sources/NSAppearance+iTerm.h b/sources/NSAppearance+iTerm.h
index 8f9942bb58..3ee21eaef5 100644
--- a/sources/NSAppearance+iTerm.h
+++ b/sources/NSAppearance+iTerm.h
@@ -18,6 +18,7 @@ NS_ASSUME_NONNULL_BEGIN
 // Converts a tab style if automatic.
 - (iTermPreferencesTabStyle)it_tabStyle:(iTermPreferencesTabStyle)tabStyle;
 + (instancetype)it_appearanceForCurrentTheme;
++ (instancetype)it_appearanceForCurrentSessionWithBackgroundColor:(nullable NSColor *)backgroundColor;
 + (void)it_performBlockWithCurrentAppearanceSetToAppearanceForCurrentTheme:(void (^)(void))block;
 - (void)it_performAsCurrentDrawingAppearance:(void (^NS_NOESCAPE)(void))block;
 
diff --git a/sources/NSAppearance+iTerm.m b/sources/NSAppearance+iTerm.m
index d1f78c6f59..a57460c2ba 100644
--- a/sources/NSAppearance+iTerm.m
+++ b/sources/NSAppearance+iTerm.m
@@ -7,6 +7,7 @@
 
 #import "NSAppearance+iTerm.h"
 #import "DebugLogging.h"
+#import "NSColor+iTerm.h"
 #import "iTermPreferences.h"
 
 @implementation NSAppearance (iTerm)
@@ -41,6 +42,25 @@ + (instancetype)it_appearanceForCurrentTheme {
     }
 }
 
++ (instancetype)it_appearanceForCurrentSessionWithBackgroundColor:(nullable NSColor *)backgroundColor {
+    iTermPreferencesTabStyle preferredStyle = [iTermPreferences intForKey:kPreferenceKeyTabStyle];
+    switch (preferredStyle) {
+        case TAB_STYLE_MINIMAL:
+        case TAB_STYLE_COMPACT:
+            if (backgroundColor) {
+                BOOL isDark = backgroundColor.perceivedBrightness < 0.5;
+                return [NSAppearance appearanceNamed:isDark ? NSAppearanceNameDarkAqua : NSAppearanceNameAqua];
+            }
+            return NSApp.effectiveAppearance;
+        case TAB_STYLE_AUTOMATIC:
+        case TAB_STYLE_LIGHT:
+        case TAB_STYLE_LIGHT_HIGH_CONTRAST:
+        case TAB_STYLE_DARK:
+        case TAB_STYLE_DARK_HIGH_CONTRAST:
+            return [self it_appearanceForCurrentTheme];
+    }
+}
+
 + (void)it_performBlockWithCurrentAppearanceSetToAppearanceForCurrentTheme:(void (^)(void))block {
     NSAppearance *appearance = [self it_appearanceForCurrentTheme];
     [appearance performAsCurrentDrawingAppearance:block];
diff --git a/sources/PTYSession.m b/sources/PTYSession.m
index 100306c76d..27d6f1278f 100644
--- a/sources/PTYSession.m
+++ b/sources/PTYSession.m
@@ -18098,6 +18098,10 @@ - (BOOL)popupWindowShouldAvoidChangingWindowOrderOnClose {
     return [iTermPreferences boolForKey:kPreferenceKeyFocusFollowsMouse] && ![self.delegate sessionBelongsToHotkeyWindow:self];
 }
 
+- (NSColor *)popupWindowBackgroundColor {
+    return self.effectiveUnprocessedBackgroundColor;
+}
+
 - (VT100Screen *)popupVT100Screen {
     return _screen;
 }
diff --git a/sources/ToastWindowController.m b/sources/ToastWindowController.m
index 74e2320b17..e5a73d6f23 100644
--- a/sources/ToastWindowController.m
+++ b/sources/ToastWindowController.m
@@ -8,7 +8,9 @@
 
 #import "ToastWindowController.h"
 #import <QuartzCore/QuartzCore.h>
+#import "NSAppearance+iTerm.h"
 #import "NSScreen+iTerm.h"
+#import "PTYSession.h"
 #import "PseudoTerminal.h"
 #import "RoundedRectView.h"
 #import "iTermController.h"
@@ -58,15 +60,19 @@ + (void)showToastWithMessage:(NSString *)message duration:(NSInteger)duration to
 + (void)showToastWithMessage:(NSString *)message duration:(NSInteger)duration screenCoordinate:(NSPoint)screenCoordinate pointSize:(CGFloat)pointSize center:(BOOL)center {
     ToastWindowController *toast = [[ToastWindowController alloc] init];
 
+    PTYSession *session = [[iTermController sharedInstance] currentTerminal].currentSession;
+    NSAppearance *sessionAppearance = [NSAppearance it_appearanceForCurrentSessionWithBackgroundColor:session.effectiveUnprocessedBackgroundColor];
+    BOOL isDark = sessionAppearance.it_isDark;
+
     NSTextField *textField = [[NSTextField alloc] init];
-    [textField setTextColor:[NSColor whiteColor]];
+    [textField setTextColor:isDark ? [NSColor whiteColor] : [NSColor blackColor]];
     [textField setBackgroundColor:[NSColor clearColor]];
     [textField setFont:[NSFont systemFontOfSize:pointSize weight:NSFontWeightMedium]];
     [textField setBordered:NO];
     [textField setStringValue:message];
     [textField setEditable:NO];
     NSShadow *textShadow = [[NSShadow alloc] init];
-    textShadow.shadowColor = [[NSColor blackColor] colorWithAlphaComponent:0.3];
+    textShadow.shadowColor = [isDark ? [NSColor blackColor] : [NSColor whiteColor] colorWithAlphaComponent:0.3];
     textShadow.shadowOffset = NSMakeSize(0, -1);
     textShadow.shadowBlurRadius = 2.0;
     [textField setShadow:textShadow];
@@ -138,8 +144,8 @@ + (void)showToastWithMessage:(NSString *)message duration:(NSInteger)duration sc
     vev.wantsLayer = YES;
     vev.blendingMode = NSVisualEffectBlendingModeBehindWindow;
     vev.state = NSVisualEffectStateActive;
-    vev.material = NSVisualEffectMaterialHUDWindow;
-    vev.appearance = [NSAppearance appearanceNamed:NSAppearanceNameVibrantDark];
+    vev.material = isDark ? NSVisualEffectMaterialHUDWindow : NSVisualEffectMaterialSheet;
+    vev.appearance = [NSAppearance appearanceNamed:isDark ? NSAppearanceNameVibrantDark : NSAppearanceNameVibrantLight];
     vev.autoresizingMask = NSViewWidthSizable | NSViewHeightSizable;
     vev.maskImage = maskImage;
     [container addSubview:vev];
diff --git a/sources/iTermGlobalSearchWindowController.m b/sources/iTermGlobalSearchWindowController.m
index 100e155038..806a9b15fc 100644
--- a/sources/iTermGlobalSearchWindowController.m
+++ b/sources/iTermGlobalSearchWindowController.m
@@ -10,6 +10,7 @@
 #import "FindContext.h"
 #import "iTerm2SharedARC-Swift.h"
 #import "iTermController.h"
+#import "NSAppearance+iTerm.h"
 #import "iTermFocusReportingTextField.h"
 #import "iTermGlobalSearchEngine.h"
 #import "iTermGlobalSearchOutlineView.h"
@@ -58,6 +59,8 @@ - (instancetype)init {
 - (void)windowDidLoad {
     self.window.delegate = self;
     self.window.level = NSFloatingWindowLevel;
+    PTYSession *session = [[iTermController sharedInstance] currentTerminal].currentSession;
+    self.window.appearance = [NSAppearance it_appearanceForCurrentSessionWithBackgroundColor:session.effectiveUnprocessedBackgroundColor];
     [_outlineView expandItem:nil expandChildren:YES];
     _panel.becomesKeyOnlyIfNeeded = YES;
     [_findType selectItemWithTag:[iTermUserDefaults globalSearchMode]];
diff --git a/sources/iTermInstantReplayWindowController.m b/sources/iTermInstantReplayWindowController.m
index 7f1c56ba6e..727e35e11f 100644
--- a/sources/iTermInstantReplayWindowController.m
+++ b/sources/iTermInstantReplayWindowController.m
@@ -9,6 +9,10 @@
 #import "iTermInstantReplayWindowController.h"
 
 #import "DebugLogging.h"
+#import "iTermController.h"
+#import "NSAppearance+iTerm.h"
+#import "PTYSession.h"
+#import "PseudoTerminal.h"
 
 static const float kAlphaValue = 0.9;
 
@@ -138,6 +142,8 @@ - (void)windowDidLoad
 
     self.window.level = NSFloatingWindowLevel;
     self.window.alphaValue = kAlphaValue;
+    PTYSession *session = [[iTermController sharedInstance] currentTerminal].currentSession;
+    self.window.appearance = [NSAppearance it_appearanceForCurrentSessionWithBackgroundColor:session.effectiveUnprocessedBackgroundColor];
 }
 
 - (void)windowWillClose:(NSNotification *)notification {
diff --git a/sources/iTermOpenQuicklyWindowController.m b/sources/iTermOpenQuicklyWindowController.m
index d6407dc206..cf77c56990 100644
--- a/sources/iTermOpenQuicklyWindowController.m
+++ b/sources/iTermOpenQuicklyWindowController.m
@@ -18,7 +18,6 @@
 #import "iTermSnippetsMenuController.h"
 #import "DebugLogging.h"
 #import "NSAppearance+iTerm.h"
-#import "NSColor+iTerm.h"
 #import "NSObject+iTerm.h"
 #import "NSTextField+iTerm.h"
 #import "NSWindow+iTerm.h"
diff --git a/sources/iTermPopupWindowController.h b/sources/iTermPopupWindowController.h
index 51c9f04575..58381c98a5 100644
--- a/sources/iTermPopupWindowController.h
+++ b/sources/iTermPopupWindowController.h
@@ -35,6 +35,9 @@
 // If the cursor is preceded by whitespace the last word will be empty. Words go in reverse order.
 - (NSArray<NSString *> *)popupWordsBeforeInsertionPoint:(int)count;
 - (BOOL)popupWindowShouldAvoidChangingWindowOrderOnClose;
+
+@optional
+- (NSColor *)popupWindowBackgroundColor;
 @end
 
 @protocol iTermPopupWindowHosting
diff --git a/sources/iTermPopupWindowController.m b/sources/iTermPopupWindowController.m
index adbdc81e74..030288eeb8 100644
--- a/sources/iTermPopupWindowController.m
+++ b/sources/iTermPopupWindowController.m
@@ -4,6 +4,8 @@
 #import "DebugLogging.h"
 #import "iTermAdvancedSettingsModel.h"
 #import "iTermPreferences.h"
+#import "NSAppearance+iTerm.h"
+#import "NSColor+iTerm.h"
 #import "NSObject+iTerm.h"
 #import "NSTextField+iTerm.h"
 #import "NSView+iTerm.h"
@@ -161,6 +163,9 @@ - (void)popWithDelegate:(id<PopupDelegate>)delegate
 
     [self.popupWindow setOwningWindow:owningWindow];
 
+    NSColor *bgColor = [delegate respondsToSelector:@selector(popupWindowBackgroundColor)] ? [delegate popupWindowBackgroundColor] : nil;
+    self.window.appearance = [NSAppearance it_appearanceForCurrentSessionWithBackgroundColor:bgColor];
+
     static const NSTimeInterval kAnimationDuration = 0.15;
     self.window.alphaValue = 0;
     if (delegate.popupWindowIsInFloatingHotkeyWindow) {
diff --git a/sources/iTermStatusBarLargeComposerViewController.m b/sources/iTermStatusBarLargeComposerViewController.m
index 4e7c299d0c..5a895adde3 100644
--- a/sources/iTermStatusBarLargeComposerViewController.m
+++ b/sources/iTermStatusBarLargeComposerViewController.m
@@ -365,6 +365,10 @@ - (BOOL)popupWindowShouldAvoidChangingWindowOrderOnClose {
     return NO;
 }
 
+- (NSColor *)popupWindowBackgroundColor {
+    return nil;
+}
+
 - (NSRect)popupScreenVisibleFrame {
     return self.view.window.screen.visibleFrame;
 }