diff --git a/quantum/action.c b/quantum/action.c
index dd82c9ec99f..f05816b7ae4 100644
--- a/quantum/action.c
+++ b/quantum/action.c
@@ -112,7 +112,7 @@ void action_exec(keyevent_t event) {
         if (has_oneshot_layer_timed_out()) {
             clear_oneshot_layer_state(ONESHOT_OTHER_KEY_PRESSED);
         }
-        if (has_oneshot_mods_timed_out()) {
+        if (has_oneshot_mods_timed_out() && !get_oneshot_mods_fired()) {
             clear_oneshot_mods();
         }
 #        ifdef SWAP_HANDS_ENABLE
diff --git a/quantum/action_util.c b/quantum/action_util.c
index e821e113ef3..e4e4566ade3 100644
--- a/quantum/action_util.c
+++ b/quantum/action_util.c
@@ -46,9 +46,13 @@ extern inline void clear_keys(void);
 #ifndef NO_ACTION_ONESHOT
 static uint8_t oneshot_mods        = 0;
 static uint8_t oneshot_locked_mods = 0;
+static bool    oneshot_mods_fired  = false;
 uint8_t        get_oneshot_locked_mods(void) {
     return oneshot_locked_mods;
 }
+bool get_oneshot_mods_fired(void) {
+    return oneshot_mods_fired;
+}
 void add_oneshot_locked_mods(uint8_t mods) {
     if ((oneshot_locked_mods & mods) != mods) {
         oneshot_locked_mods |= mods;
@@ -260,16 +264,15 @@ static uint8_t get_mods_for_report(void) {
 
 #ifndef NO_ACTION_ONESHOT
     if (oneshot_mods) {
-#    if (defined(ONESHOT_TIMEOUT) && (ONESHOT_TIMEOUT > 0))
-        if (has_oneshot_mods_timed_out()) {
-            dprintf("Oneshot: timeout\n");
+        // Fire oneshots when other keys are pressed
+        // Release oneshots when everything else is released
+        if (has_anykey() || mods) {
+            oneshot_mods_fired = true;
+        } else if (oneshot_mods_fired) {
+            oneshot_mods_fired = false;
             clear_oneshot_mods();
         }
-#    endif
         mods |= oneshot_mods;
-        if (has_anykey()) {
-            clear_oneshot_mods();
-        }
     }
 #endif
 
diff --git a/quantum/action_util.h b/quantum/action_util.h
index d2ecb145bed..967d9a1c5e1 100644
--- a/quantum/action_util.h
+++ b/quantum/action_util.h
@@ -68,6 +68,7 @@ void    clear_oneshot_mods(void);
 bool    has_oneshot_mods_timed_out(void);
 
 uint8_t get_oneshot_locked_mods(void);
+bool    get_oneshot_mods_fired(void);
 void    add_oneshot_locked_mods(uint8_t mods);
 void    set_oneshot_locked_mods(uint8_t mods);
 void    clear_oneshot_locked_mods(void);
diff --git a/tests/basic/config.h b/tests/basic/config.h
index 7fc76d7c2e7..9b00608b12a 100644
--- a/tests/basic/config.h
+++ b/tests/basic/config.h
@@ -17,3 +17,5 @@
 #pragma once
 
 #include "test_common.h"
+
+#define ONESHOT_TAP_TOGGLE 5
diff --git a/tests/basic/test_one_shot_keys.cpp b/tests/basic/test_one_shot_keys.cpp
index 4784c866940..fdae638b7cd 100644
--- a/tests/basic/test_one_shot_keys.cpp
+++ b/tests/basic/test_one_shot_keys.cpp
@@ -254,7 +254,7 @@ TEST_F(OneShot, OSMHoldNotLockingOSMs) {
 
     /* Press and release regular key */
     EXPECT_REPORT(driver, (osm_key1.report_code, osm_key2.report_code, regular_key.report_code)).Times(1);
-    EXPECT_REPORT(driver, (osm_key2.report_code)).Times(1);
+    EXPECT_REPORT(driver, (osm_key1.report_code, osm_key2.report_code)).Times(1);
     tap_key(regular_key);
     VERIFY_AND_CLEAR(driver);
 
@@ -277,6 +277,118 @@ TEST_F(OneShot, OSMHoldNotLockingOSMs) {
     VERIFY_AND_CLEAR(driver);
 }
 
+TEST_F(OneShot, OSMHoldRelease) {
+    TestDriver driver;
+    InSequence s;
+    KeymapKey  osm_key = KeymapKey{0, 0, 0, OSM(MOD_LSFT), KC_LSFT};
+
+    set_keymap({osm_key});
+
+    /* Press and release OSM */
+    EXPECT_NO_REPORT(driver);
+    tap_key(osm_key);
+    idle_for(TAPPING_TERM);
+    VERIFY_AND_CLEAR(driver);
+
+    /* Press and hold OSM */
+    EXPECT_REPORT(driver, (osm_key.report_code)).Times(1);
+    osm_key.press();
+    run_one_scan_loop();
+    idle_for(TAPPING_TERM);
+    VERIFY_AND_CLEAR(driver);
+
+    /* Release OSM */
+    EXPECT_EMPTY_REPORT(driver);
+    osm_key.release();
+    run_one_scan_loop();
+    VERIFY_AND_CLEAR(driver);
+}
+
+TEST_F(OneShot, OSMHoldReleaseTwoOSMs) {
+    TestDriver driver;
+    InSequence s;
+    KeymapKey  osm_key1 = KeymapKey{0, 0, 0, OSM(MOD_LSFT), KC_LSFT};
+    KeymapKey  osm_key2 = KeymapKey{0, 0, 1, OSM(MOD_LCTL), KC_LCTL};
+
+    set_keymap({osm_key1, osm_key2});
+
+    /* Press and release OSM1 */
+    EXPECT_NO_REPORT(driver);
+    tap_key(osm_key1);
+    VERIFY_AND_CLEAR(driver);
+
+    /* Press and release OSM2 */
+    EXPECT_NO_REPORT(driver);
+    tap_key(osm_key2);
+    idle_for(TAPPING_TERM);
+    VERIFY_AND_CLEAR(driver);
+
+    /* Press and hold OSM1 */
+    EXPECT_REPORT(driver, (osm_key1.report_code, osm_key2.report_code)).Times(1);
+    osm_key1.press();
+    run_one_scan_loop();
+    idle_for(TAPPING_TERM);
+    VERIFY_AND_CLEAR(driver);
+
+    /* Release OSM1 */
+    EXPECT_EMPTY_REPORT(driver);
+    osm_key1.release();
+    run_one_scan_loop();
+    VERIFY_AND_CLEAR(driver);
+}
+
+TEST_F(OneShot, OSMNonOSMMod) {
+    TestDriver driver;
+    InSequence s;
+    KeymapKey  osm_key     = KeymapKey{0, 0, 0, OSM(MOD_LSFT), KC_LSFT};
+    KeymapKey  regular_mod = KeymapKey{0, 1, 0, KC_LCTL};
+
+    set_keymap({osm_key, regular_mod});
+
+    /* Press and release OSM */
+    EXPECT_NO_REPORT(driver);
+    tap_key(osm_key);
+    VERIFY_AND_CLEAR(driver);
+
+    /* Press regular mod */
+    EXPECT_REPORT(driver, (osm_key.report_code, regular_mod.report_code)).Times(1);
+    regular_mod.press();
+    run_one_scan_loop();
+    idle_for(TAPPING_TERM);
+    VERIFY_AND_CLEAR(driver);
+
+    /* Release regular mod */
+    EXPECT_EMPTY_REPORT(driver);
+    regular_mod.release();
+    run_one_scan_loop();
+    VERIFY_AND_CLEAR(driver);
+}
+
+TEST_F(OneShot, OSMLockRelease) {
+    TestDriver driver;
+    InSequence s;
+    KeymapKey  osm_key = KeymapKey{0, 0, 0, OSM(MOD_LSFT), KC_LSFT};
+
+    set_keymap({osm_key});
+
+    EXPECT_NO_REPORT(driver);
+    for (int i = 1; i < ONESHOT_TAP_TOGGLE; i++) {
+        /* Press and release OSM */
+        tap_key(osm_key);
+    }
+    VERIFY_AND_CLEAR(driver);
+
+    /* Lock OSM */
+    EXPECT_REPORT(driver, (osm_key.report_code)).Times(1);
+    tap_key(osm_key);
+    VERIFY_AND_CLEAR(driver);
+
+    /* Unlock OSM */
+    EXPECT_NO_REPORT(driver);
+    tap_key(osm_key);
+    VERIFY_AND_CLEAR(driver);
+}
+
 TEST_F(OneShot, OSLWithAdditionalKeypress) {
     TestDriver driver;
     InSequence s;