diff --git a/CHANGES b/CHANGES
index ab4785fa2..4e82bc981 100644
--- a/CHANGES
+++ b/CHANGES
@@ -56,6 +56,7 @@ Other fixes:
  - Core: Fix the runloop resuming after a game has crashed (fixes mgba.io/i/2451)
  - Core: Fix crash if library can't be opened
  - Debugger: Fix crash with extremely long CLI strings
+ - Debugger: Fix multiple conditional watchpoints at the same address
  - FFmpeg: Fix crash when encoding audio with some containers
  - FFmpeg: Fix GIF recording (fixes mgba.io/i/2393)
  - GB: Fix temporary saves
diff --git a/src/arm/debugger/memory-debugger.c b/src/arm/debugger/memory-debugger.c
index 8ccb592e7..68b4b4175 100644
--- a/src/arm/debugger/memory-debugger.c
+++ b/src/arm/debugger/memory-debugger.c
@@ -102,7 +102,7 @@ static bool _checkWatchpoints(struct ARMDebugger* debugger, uint32_t address, st
 				int32_t value;
 				int segment;
 				if (!mDebuggerEvaluateParseTree(debugger->d.p, watchpoint->condition, &value, &segment) || !(value || segment >= 0)) {
-					return false;
+					continue;
 				}
 			}
 
diff --git a/src/sm83/debugger/memory-debugger.c b/src/sm83/debugger/memory-debugger.c
index 2cd81669e..e0a48553f 100644
--- a/src/sm83/debugger/memory-debugger.c
+++ b/src/sm83/debugger/memory-debugger.c
@@ -52,7 +52,7 @@ static bool _checkWatchpoints(struct SM83Debugger* debugger, uint16_t address, s
 				int32_t value;
 				int segment;
 				if (!mDebuggerEvaluateParseTree(debugger->d.p, watchpoint->condition, &value, &segment) || !(value || segment >= 0)) {
-					return false;
+					continue;
 				}
 			}
 			uint8_t oldValue = debugger->originalMemory.load8(debugger->cpu, address);