diff --git a/app/assets/javascripts/pretty-text/addon/emoji/data.js b/app/assets/javascripts/pretty-text/addon/emoji/data.js
index 79be4c5e18c..f23158ec227 100644
--- a/app/assets/javascripts/pretty-text/addon/emoji/data.js
+++ b/app/assets/javascripts/pretty-text/addon/emoji/data.js
@@ -8,7 +8,7 @@ export const emojis = [
   "joy",
   "rofl",
   "smiley",
-  "smile",
+  "grinning_face_with_smiling_eyes",
   "sweat_smile",
   "laughing",
   "innocent",
@@ -61,6 +61,7 @@ export const emojis = [
   "cold_sweat",
   "hushed",
   "frowning",
+  "frowning_face_with_open_mouth",
   "anguished",
   "cry",
   "disappointed_relieved",
@@ -1919,6 +1920,7 @@ export const aliases = {
     "white_sun_rain_cloud",
     "white_sun_behind_cloud_with_rain",
   ],
+  grinning_face_with_smiling_eyes: ["smile"],
   partly_sunny: ["white_sun_small_cloud", "white_sun_with_small_cloud"],
   open_umbrella: ["umbrella2"],
   hammer_and_wrench: ["tools"],
@@ -2073,7 +2075,7 @@ export const replacements = {
   "😂": "joy",
   "🤣": "rofl",
   "😃": "smiley",
-  "😄": "smile",
+  "😄": "grinning_face_with_smiling_eyes",
   "😅": "sweat_smile",
   "😆": "laughing",
   "😇": "innocent",
@@ -2113,8 +2115,8 @@ export const replacements = {
   "😡": "rage",
   "😔": "pensive",
   "😕": "confused",
-  "🙁": "slightly_frowning_face",
-  "☹": "frowning",
+  "☹️": "slightly_frowning_face",
+  "🙁": "frowning",
   "😣": "persevere",
   "😖": "confounded",
   "😫": "tired_face",
@@ -2125,7 +2127,7 @@ export const replacements = {
   "😨": "fearful",
   "😰": "cold_sweat",
   "😯": "hushed",
-  "😦": "frowning",
+  "😦": "frowning_face_with_open_mouth",
   "😧": "anguished",
   "😢": "cry",
   "😥": "disappointed_relieved",
@@ -4549,6 +4551,7 @@ export const replacements = {
   "🤍": "white_heart",
   "🤎": "brown_heart",
   "🏳️‍⚧": "transgender_flag",
+  "☹": "frowning",
   "☻": "slight_smile",
   "♡": "heart",
 };
diff --git a/lib/emoji/db.json b/lib/emoji/db.json
index ce808c9e8ad..5f7c778fd2d 100644
--- a/lib/emoji/db.json
+++ b/lib/emoji/db.json
@@ -26,7 +26,7 @@
     },
     {
       "code": "1f604",
-      "name": "smile"
+      "name": "grinning_face_with_smiling_eyes"
     },
     {
       "code": "1f605",
@@ -185,11 +185,11 @@
       "name": "confused"
     },
     {
-      "code": "1f641",
+      "code": "2639-fe0f",
       "name": "slightly_frowning_face"
     },
     {
-      "code": "2639",
+      "code": "1f641",
       "name": "frowning_face"
     },
     {
@@ -233,9 +233,13 @@
       "name": "hushed"
     },
     {
-      "code": "1f626",
+      "code": "1f641",
       "name": "frowning"
     },
+    {
+      "code": "1f626",
+      "name": "frowning_face_with_open_mouth"
+    },
     {
       "code": "1f627",
       "name": "anguished"
@@ -6794,607 +6798,205 @@
     "palms_up_together"
   ],
   "aliases": {
-    "right_anger_bubble": [
-      "anger_right"
-    ],
-    "ballot_box": [
-      "ballot_box_with_ballot"
-    ],
-    "basketball_man": [
-      "basketball_player",
-      "person_with_ball"
-    ],
-    "beach_umbrella": [
-      "umbrella_on_ground",
-      "beach",
-      "beach_with_umbrella"
-    ],
-    "parasol_on_ground": [
-      "umbrella_on_ground"
-    ],
-    "bellhop_bell": [
-      "bellhop"
-    ],
-    "biohazard": [
-      "biohazard_sign"
-    ],
-    "bow_and_arrow": [
-      "archery"
-    ],
-    "spiral_calendar": [
-      "calendar_spiral",
-      "spiral_calendar_pad"
-    ],
-    "card_file_box": [
-      "card_box"
-    ],
-    "champagne": [
-      "bottle_with_popping_cork"
-    ],
-    "cheese": [
-      "cheese_wedge"
-    ],
-    "city_sunset": [
-      "city_dusk"
-    ],
-    "couch_and_lamp": [
-      "couch"
-    ],
-    "crayon": [
-      "lower_left_crayon"
-    ],
-    "cricket_bat_and_ball": [
-      "cricket_bat_ball"
-    ],
-    "latin_cross": [
-      "cross"
-    ],
-    "dagger": [
-      "dagger_knife"
-    ],
-    "desktop_computer": [
-      "desktop"
-    ],
-    "card_index_dividers": [
-      "dividers"
-    ],
-    "dove": [
-      "dove_of_peace"
-    ],
-    "footprints": [
-      "feet"
-    ],
-    "fire": [
-      "flame"
-    ],
-    "black_flag": [
-      "flag_black",
-      "waving_black_flag"
-    ],
-    "cn": [
-      "flag_cn"
-    ],
-    "de": [
-      "flag_de"
-    ],
-    "es": [
-      "flag_es"
-    ],
-    "fr": [
-      "flag_fr"
-    ],
-    "uk": [
-      "gb",
-      "flag_gb"
-    ],
-    "it": [
-      "flag_it"
-    ],
-    "jp": [
-      "flag_jp"
-    ],
-    "kr": [
-      "flag_kr"
-    ],
-    "ru": [
-      "flag_ru"
-    ],
-    "us": [
-      "flag_us"
-    ],
-    "white_flag": [
-      "flag_white",
-      "waving_white_flag"
-    ],
-    "plate_with_cutlery": [
-      "fork_knife_plate",
-      "fork_and_knife_with_plate"
-    ],
-    "framed_picture": [
-      "frame_photo",
-      "frame_with_picture"
-    ],
-    "hammer_and_pick": [
-      "hammer_pick"
-    ],
+    "right_anger_bubble": ["anger_right"],
+    "ballot_box": ["ballot_box_with_ballot"],
+    "basketball_man": ["basketball_player", "person_with_ball"],
+    "beach_umbrella": ["umbrella_on_ground", "beach", "beach_with_umbrella"],
+    "parasol_on_ground": ["umbrella_on_ground"],
+    "bellhop_bell": ["bellhop"],
+    "biohazard": ["biohazard_sign"],
+    "bow_and_arrow": ["archery"],
+    "spiral_calendar": ["calendar_spiral", "spiral_calendar_pad"],
+    "card_file_box": ["card_box"],
+    "champagne": ["bottle_with_popping_cork"],
+    "cheese": ["cheese_wedge"],
+    "city_sunset": ["city_dusk"],
+    "couch_and_lamp": ["couch"],
+    "crayon": ["lower_left_crayon"],
+    "cricket_bat_and_ball": ["cricket_bat_ball"],
+    "latin_cross": ["cross"],
+    "dagger": ["dagger_knife"],
+    "desktop_computer": ["desktop"],
+    "card_index_dividers": ["dividers"],
+    "dove": ["dove_of_peace"],
+    "footprints": ["feet"],
+    "fire": ["flame"],
+    "black_flag": ["flag_black", "waving_black_flag"],
+    "cn": ["flag_cn"],
+    "de": ["flag_de"],
+    "es": ["flag_es"],
+    "fr": ["flag_fr"],
+    "uk": ["gb", "flag_gb"],
+    "it": ["flag_it"],
+    "jp": ["flag_jp"],
+    "kr": ["flag_kr"],
+    "ru": ["flag_ru"],
+    "us": ["flag_us"],
+    "white_flag": ["flag_white", "waving_white_flag"],
+    "plate_with_cutlery": ["fork_knife_plate", "fork_and_knife_with_plate"],
+    "framed_picture": ["frame_photo", "frame_with_picture"],
+    "hammer_and_pick": ["hammer_pick"],
     "heavy_heart_exclamation": [
       "heart_exclamation",
       "heavy_heart_exclamation_mark_ornament"
     ],
-    "houses": [
-      "homes",
-      "house_buildings"
-    ],
-    "hotdog": [
-      "hot_dog"
-    ],
-    "derelict_house": [
-      "house_abandoned",
-      "derelict_house_building"
-    ],
-    "desert_island": [
-      "island"
-    ],
-    "old_key": [
-      "key2"
-    ],
-    "laughing": [
-      "satisfied"
-    ],
-    "business_suit_levitating": [
-      "levitate",
-      "man_in_business_suit_levitating"
-    ],
-    "weight_lifting_man": [
-      "lifter",
-      "weight_lifter"
-    ],
-    "medal_sports": [
-      "medal",
-      "sports_medal"
-    ],
-    "metal": [
-      "sign_of_the_horns"
-    ],
-    "fu": [
-      "middle_finger",
-      "reversed_hand_with_middle_finger_extended"
-    ],
-    "motorcycle": [
-      "racing_motorcycle"
-    ],
-    "mountain_snow": [
-      "snow_capped_mountain"
-    ],
-    "newspaper_roll": [
-      "newspaper2",
-      "rolled_up_newspaper"
-    ],
-    "spiral_notepad": [
-      "notepad_spiral",
-      "spiral_note_pad"
-    ],
-    "oil_drum": [
-      "oil"
-    ],
-    "older_woman": [
-      "grandma"
-    ],
-    "paintbrush": [
-      "lower_left_paintbrush"
-    ],
-    "paperclips": [
-      "linked_paperclips"
-    ],
-    "pause_button": [
-      "double_vertical_bar"
-    ],
-    "peace_symbol": [
-      "peace"
-    ],
-    "fountain_pen": [
-      "pen_fountain",
-      "lower_left_fountain_pen"
-    ],
-    "ping_pong": [
-      "table_tennis"
-    ],
-    "place_of_worship": [
-      "worship_symbol"
-    ],
-    "poop": [
-      "shit",
-      "hankey",
-      "poo"
-    ],
-    "radioactive": [
-      "radioactive_sign"
-    ],
-    "railway_track": [
-      "railroad_track"
-    ],
-    "robot": [
-      "robot_face"
-    ],
-    "skull": [
-      "skeleton"
-    ],
-    "skull_and_crossbones": [
-      "skull_crossbones"
-    ],
-    "speaking_head": [
-      "speaking_head_in_silhouette"
-    ],
-    "male_detective": [
-      "spy",
-      "sleuth_or_spy"
-    ],
-    "thinking": [
-      "thinking_face"
-    ],
-    "-1": [
-      "thumbsdown"
-    ],
-    "+1": [
-      "thumbsup"
-    ],
+    "houses": ["homes", "house_buildings"],
+    "hotdog": ["hot_dog"],
+    "derelict_house": ["house_abandoned", "derelict_house_building"],
+    "desert_island": ["island"],
+    "old_key": ["key2"],
+    "laughing": ["satisfied"],
+    "business_suit_levitating": ["levitate", "man_in_business_suit_levitating"],
+    "weight_lifting_man": ["lifter", "weight_lifter"],
+    "medal_sports": ["medal", "sports_medal"],
+    "metal": ["sign_of_the_horns"],
+    "fu": ["middle_finger", "reversed_hand_with_middle_finger_extended"],
+    "motorcycle": ["racing_motorcycle"],
+    "mountain_snow": ["snow_capped_mountain"],
+    "newspaper_roll": ["newspaper2", "rolled_up_newspaper"],
+    "spiral_notepad": ["notepad_spiral", "spiral_note_pad"],
+    "oil_drum": ["oil"],
+    "older_woman": ["grandma"],
+    "paintbrush": ["lower_left_paintbrush"],
+    "paperclips": ["linked_paperclips"],
+    "pause_button": ["double_vertical_bar"],
+    "peace_symbol": ["peace"],
+    "fountain_pen": ["pen_fountain", "lower_left_fountain_pen"],
+    "ping_pong": ["table_tennis"],
+    "place_of_worship": ["worship_symbol"],
+    "poop": ["shit", "hankey", "poo"],
+    "radioactive": ["radioactive_sign"],
+    "railway_track": ["railroad_track"],
+    "robot": ["robot_face"],
+    "skull": ["skeleton"],
+    "skull_and_crossbones": ["skull_crossbones"],
+    "speaking_head": ["speaking_head_in_silhouette"],
+    "male_detective": ["spy", "sleuth_or_spy"],
+    "thinking": ["thinking_face"],
+    "-1": ["thumbsdown"],
+    "+1": ["thumbsup"],
     "cloud_with_lightning_and_rain": [
       "thunder_cloud_rain",
       "thunder_cloud_and_rain"
     ],
-    "tickets": [
-      "admission_tickets"
-    ],
-    "next_track_button": [
-      "track_next",
-      "next_track"
-    ],
-    "previous_track_button": [
-      "track_previous",
-      "previous_track"
-    ],
-    "unicorn": [
-      "unicorn_face"
-    ],
-    "funeral_urn": [
-      "urn"
-    ],
-    "sun_behind_large_cloud": [
-      "white_sun_cloud",
-      "white_sun_behind_cloud"
-    ],
+    "tickets": ["admission_tickets"],
+    "next_track_button": ["track_next", "next_track"],
+    "previous_track_button": ["track_previous", "previous_track"],
+    "unicorn": ["unicorn_face"],
+    "funeral_urn": ["urn"],
+    "sun_behind_large_cloud": ["white_sun_cloud", "white_sun_behind_cloud"],
     "sun_behind_rain_cloud": [
       "white_sun_rain_cloud",
       "white_sun_behind_cloud_with_rain"
     ],
-    "partly_sunny": [
-      "white_sun_small_cloud",
-      "white_sun_with_small_cloud"
-    ],
-    "open_umbrella": [
-      "umbrella2"
-    ],
-    "hammer_and_wrench": [
-      "tools"
-    ],
-    "face_with_thermometer": [
-      "thermometer_face"
-    ],
-    "timer_clock": [
-      "timer"
-    ],
-    "keycap_ten": [
-      "ten"
-    ],
-    "memo": [
-      "pencil"
-    ],
-    "rescue_worker_helmet": [
-      "helmet_with_cross",
-      "helmet_with_white_cross"
-    ],
-    "slightly_smiling_face": [
-      "slightly_smiling",
-      "slight_smile"
-    ],
-    "construction_worker_man": [
-      "construction_worker"
-    ],
-    "upside_down_face": [
-      "upside_down"
-    ],
-    "money_mouth_face": [
-      "money_mouth"
-    ],
-    "nerd_face": [
-      "nerd"
-    ],
-    "hugs": [
-      "hugging",
-      "hugging_face"
-    ],
-    "roll_eyes": [
-      "rolling_eyes",
-      "face_with_rolling_eyes"
-    ],
-    "slightly_frowning_face": [
-      "slight_frown"
-    ],
-    "frowning_face": [
-      "frowning2",
-      "white_frowning_face"
-    ],
-    "zipper_mouth_face": [
-      "zipper_mouth"
-    ],
-    "face_with_head_bandage": [
-      "head_bandage"
-    ],
-    "raised_hand_with_fingers_splayed": [
-      "hand_splayed"
-    ],
-    "raised_hand": [
-      "hand"
-    ],
+    "partly_sunny": ["white_sun_small_cloud", "white_sun_with_small_cloud"],
+    "open_umbrella": ["umbrella2"],
+    "hammer_and_wrench": ["tools"],
+    "face_with_thermometer": ["thermometer_face"],
+    "timer_clock": ["timer"],
+    "keycap_ten": ["ten"],
+    "memo": ["pencil"],
+    "rescue_worker_helmet": ["helmet_with_cross", "helmet_with_white_cross"],
+    "slightly_smiling_face": ["slightly_smiling", "slight_smile"],
+    "construction_worker_man": ["construction_worker"],
+    "upside_down_face": ["upside_down"],
+    "money_mouth_face": ["money_mouth"],
+    "nerd_face": ["nerd"],
+    "hugs": ["hugging", "hugging_face"],
+    "roll_eyes": ["rolling_eyes", "face_with_rolling_eyes"],
+    "slightly_frowning_face": ["slight_frown"],
+    "frowning_face": ["frowning2", "white_frowning_face"],
+    "zipper_mouth_face": ["zipper_mouth"],
+    "face_with_head_bandage": ["head_bandage"],
+    "raised_hand_with_fingers_splayed": ["hand_splayed"],
+    "raised_hand": ["hand"],
     "vulcan_salute": [
       "vulcan",
       "raised_hand_with_part_between_middle_and_ring_fingers"
     ],
-    "policeman": [
-      "cop"
-    ],
-    "running_man": [
-      "runner"
-    ],
-    "walking_man": [
-      "walking"
-    ],
-    "bowing_man": [
-      "bow"
-    ],
-    "no_good_woman": [
-      "no_good"
-    ],
-    "raising_hand_woman": [
-      "raising_hand"
-    ],
-    "pouting_woman": [
-      "person_with_pouting_face"
-    ],
-    "frowning_woman": [
-      "person_frowning"
-    ],
-    "haircut_woman": [
-      "haircut"
-    ],
-    "massage_woman": [
-      "massage"
-    ],
-    "tshirt": [
-      "shirt"
-    ],
-    "biking_man": [
-      "bicyclist"
-    ],
-    "mountain_biking_man": [
-      "mountain_bicyclist"
-    ],
-    "passenger_ship": [
-      "cruise_ship"
-    ],
-    "motor_boat": [
-      "motorboat",
-      "boat"
-    ],
-    "flight_arrival": [
-      "airplane_arriving"
-    ],
-    "flight_departure": [
-      "airplane_departure"
-    ],
-    "small_airplane": [
-      "airplane_small"
-    ],
-    "racing_car": [
-      "race_car"
-    ],
-    "family_man_woman_boy_boy": [
-      "family_man_woman_boys"
-    ],
-    "family_man_woman_girl_girl": [
-      "family_man_woman_girls"
-    ],
-    "family_woman_woman_boy": [
-      "family_women_boy"
-    ],
-    "family_woman_woman_girl": [
-      "family_women_girl"
-    ],
-    "family_woman_woman_girl_boy": [
-      "family_women_girl_boy"
-    ],
-    "family_woman_woman_boy_boy": [
-      "family_women_boys"
-    ],
-    "family_woman_woman_girl_girl": [
-      "family_women_girls"
-    ],
-    "family_man_man_boy": [
-      "family_men_boy"
-    ],
-    "family_man_man_girl": [
-      "family_men_girl"
-    ],
-    "family_man_man_girl_boy": [
-      "family_men_girl_boy"
-    ],
-    "family_man_man_boy_boy": [
-      "family_men_boys"
-    ],
-    "family_man_man_girl_girl": [
-      "family_men_girls"
-    ],
-    "cloud_with_lightning": [
-      "cloud_lightning"
-    ],
-    "tornado": [
-      "cloud_tornado",
-      "cloud_with_tornado"
-    ],
-    "cloud_with_rain": [
-      "cloud_rain"
-    ],
-    "cloud_with_snow": [
-      "cloud_snow"
-    ],
-    "asterisk": [
-      "keycap_star"
-    ],
-    "studio_microphone": [
-      "microphone2"
-    ],
-    "medal_military": [
-      "military_medal"
-    ],
-    "couple_with_heart_woman_woman": [
-      "female_couple_with_heart"
-    ],
-    "couple_with_heart_man_man": [
-      "male_couple_with_heart"
-    ],
-    "couplekiss_woman_woman": [
-      "female_couplekiss"
-    ],
-    "couplekiss_man_man": [
-      "male_couplekiss"
-    ],
-    "honeybee": [
-      "bee"
-    ],
-    "lion": [
-      "lion_face"
-    ],
-    "artificial_satellite": [
-      "satellite_orbital"
-    ],
-    "computer_mouse": [
-      "mouse_three_button",
-      "three_button_mouse"
-    ],
-    "hocho": [
-      "knife"
-    ],
-    "swimming_man": [
-      "swimmer"
-    ],
-    "wind_face": [
-      "wind_blowing_face"
-    ],
-    "golfing_man": [
-      "golfer"
-    ],
-    "facepunch": [
-      "punch"
-    ],
-    "building_construction": [
-      "construction_site"
-    ],
-    "family_man_woman_girl_boy": [
-      "family"
-    ],
-    "ice_hockey": [
-      "hockey"
-    ],
-    "snowman_with_snow": [
-      "snowman2"
-    ],
-    "play_or_pause_button": [
-      "play_pause"
-    ],
-    "film_projector": [
-      "projector"
-    ],
-    "shopping": [
-      "shopping_bags"
-    ],
-    "open_book": [
-      "book"
-    ],
-    "national_park": [
-      "park"
-    ],
-    "world_map": [
-      "map"
-    ],
-    "pen": [
-      "pen_ballpoint",
-      "lower_left_ballpoint_pen"
-    ],
-    "email": [
-      "envelope",
-      "e-mail"
-    ],
-    "phone": [
-      "telephone"
-    ],
-    "atom_symbol": [
-      "atom"
-    ],
-    "mantelpiece_clock": [
-      "clock"
-    ],
-    "camera_flash": [
-      "camera_with_flash"
-    ],
-    "film_strip": [
-      "film_frames"
-    ],
-    "balance_scale": [
-      "scales"
-    ],
-    "surfing_man": [
-      "surfer"
-    ],
-    "couplekiss_man_woman": [
-      "couplekiss"
-    ],
-    "couple_with_heart_woman_man": [
-      "couple_with_heart"
-    ],
-    "clamp": [
-      "compression"
-    ],
-    "dancing_women": [
-      "dancers"
-    ],
-    "blonde_man": [
-      "person_with_blond_hair"
-    ],
-    "sleeping_bed": [
-      "sleeping_accommodation"
-    ],
-    "om": [
-      "om_symbol"
-    ],
-    "tipping_hand_woman": [
-      "information_desk_person"
-    ],
-    "rowing_man": [
-      "rowboat"
-    ],
-    "new_moon": [
-      "moon"
-    ],
-    "oncoming_automobile": [
-      "car",
-      "automobile"
-    ],
-    "fleur_de_lis": [
-      "fleur-de-lis"
-    ],
-    "face_vomiting": [
-      "puke"
-    ]
+    "policeman": ["cop"],
+    "running_man": ["runner"],
+    "walking_man": ["walking"],
+    "bowing_man": ["bow"],
+    "no_good_woman": ["no_good"],
+    "raising_hand_woman": ["raising_hand"],
+    "pouting_woman": ["person_with_pouting_face"],
+    "frowning_woman": ["person_frowning"],
+    "haircut_woman": ["haircut"],
+    "massage_woman": ["massage"],
+    "tshirt": ["shirt"],
+    "biking_man": ["bicyclist"],
+    "mountain_biking_man": ["mountain_bicyclist"],
+    "passenger_ship": ["cruise_ship"],
+    "motor_boat": ["motorboat", "boat"],
+    "flight_arrival": ["airplane_arriving"],
+    "flight_departure": ["airplane_departure"],
+    "small_airplane": ["airplane_small"],
+    "racing_car": ["race_car"],
+    "family_man_woman_boy_boy": ["family_man_woman_boys"],
+    "family_man_woman_girl_girl": ["family_man_woman_girls"],
+    "family_woman_woman_boy": ["family_women_boy"],
+    "family_woman_woman_girl": ["family_women_girl"],
+    "family_woman_woman_girl_boy": ["family_women_girl_boy"],
+    "family_woman_woman_boy_boy": ["family_women_boys"],
+    "family_woman_woman_girl_girl": ["family_women_girls"],
+    "family_man_man_boy": ["family_men_boy"],
+    "family_man_man_girl": ["family_men_girl"],
+    "family_man_man_girl_boy": ["family_men_girl_boy"],
+    "family_man_man_boy_boy": ["family_men_boys"],
+    "family_man_man_girl_girl": ["family_men_girls"],
+    "cloud_with_lightning": ["cloud_lightning"],
+    "tornado": ["cloud_tornado", "cloud_with_tornado"],
+    "cloud_with_rain": ["cloud_rain"],
+    "cloud_with_snow": ["cloud_snow"],
+    "asterisk": ["keycap_star"],
+    "studio_microphone": ["microphone2"],
+    "medal_military": ["military_medal"],
+    "couple_with_heart_woman_woman": ["female_couple_with_heart"],
+    "couple_with_heart_man_man": ["male_couple_with_heart"],
+    "couplekiss_woman_woman": ["female_couplekiss"],
+    "couplekiss_man_man": ["male_couplekiss"],
+    "honeybee": ["bee"],
+    "lion": ["lion_face"],
+    "artificial_satellite": ["satellite_orbital"],
+    "computer_mouse": ["mouse_three_button", "three_button_mouse"],
+    "hocho": ["knife"],
+    "swimming_man": ["swimmer"],
+    "wind_face": ["wind_blowing_face"],
+    "golfing_man": ["golfer"],
+    "facepunch": ["punch"],
+    "building_construction": ["construction_site"],
+    "family_man_woman_girl_boy": ["family"],
+    "ice_hockey": ["hockey"],
+    "snowman_with_snow": ["snowman2"],
+    "play_or_pause_button": ["play_pause"],
+    "film_projector": ["projector"],
+    "shopping": ["shopping_bags"],
+    "open_book": ["book"],
+    "national_park": ["park"],
+    "world_map": ["map"],
+    "pen": ["pen_ballpoint", "lower_left_ballpoint_pen"],
+    "email": ["envelope", "e-mail"],
+    "phone": ["telephone"],
+    "atom_symbol": ["atom"],
+    "mantelpiece_clock": ["clock"],
+    "camera_flash": ["camera_with_flash"],
+    "film_strip": ["film_frames"],
+    "balance_scale": ["scales"],
+    "surfing_man": ["surfer"],
+    "couplekiss_man_woman": ["couplekiss"],
+    "couple_with_heart_woman_man": ["couple_with_heart"],
+    "clamp": ["compression"],
+    "dancing_women": ["dancers"],
+    "blonde_man": ["person_with_blond_hair"],
+    "sleeping_bed": ["sleeping_accommodation"],
+    "om": ["om_symbol"],
+    "tipping_hand_woman": ["information_desk_person"],
+    "rowing_man": ["rowboat"],
+    "new_moon": ["moon"],
+    "oncoming_automobile": ["car", "automobile"],
+    "fleur_de_lis": ["fleur-de-lis"],
+    "face_vomiting": ["puke"]
   },
   "searchAliases": {
     "sad": [
@@ -7404,9 +7006,7 @@
       "crying_cat_face",
       "cry"
     ],
-    "cry": [
-      "sob"
-    ]
+    "cry": ["sob"]
   },
   "translations": {
     ":)": "slight_smile",
@@ -7436,4 +7036,4 @@
     ":$": "blush",
     ":-$": "blush"
   }
-}
\ No newline at end of file
+}
diff --git a/lib/emoji/groups.json b/lib/emoji/groups.json
index 9fe4b12da3f..0c18098ddaa 100644
--- a/lib/emoji/groups.json
+++ b/lib/emoji/groups.json
@@ -12,7 +12,7 @@
         "diversity": false
       },
       {
-        "name": "smile",
+        "name": "grinning_face_with_smiling_eyes",
         "diversity": false
       },
       {
@@ -291,6 +291,10 @@
         "name": "frowning",
         "diversity": false
       },
+      {
+        "name": "frowning_face_with_open_mouth",
+        "diversity": false
+      },
       {
         "name": "anguished",
         "diversity": false
@@ -6673,4 +6677,4 @@
       }
     ]
   }
-]
\ No newline at end of file
+]
diff --git a/public/images/emoji/apple/grinning_face_with_smiling_eyes.png b/public/images/emoji/apple/grinning_face_with_smiling_eyes.png
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index 00000000000..e7ef74d9b3c
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index 00000000000..1ef1cd352dc
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