diff --git a/lib/icinga/apiactions.cpp b/lib/icinga/apiactions.cpp
index 0d0422377..885834edc 100644
--- a/lib/icinga/apiactions.cpp
+++ b/lib/icinga/apiactions.cpp
@@ -288,7 +288,7 @@ Dictionary::Ptr ApiActions::RemoveAcknowledgement(const ConfigObject::Ptr& objec
 	String removedBy (HttpUtility::GetLastParameter(params, "author"));
 
 	checkable->ClearAcknowledgement(removedBy);
-	checkable->RemoveCommentsByType(CommentAcknowledgement, removedBy);
+	checkable->RemoveAckComments(removedBy);
 
 	return ApiActions::CreateResult(200, "Successfully removed acknowledgement for object '" + checkable->GetName() + "'.");
 }
diff --git a/lib/icinga/checkable-check.cpp b/lib/icinga/checkable-check.cpp
index 83c39e923..efa9477a2 100644
--- a/lib/icinga/checkable-check.cpp
+++ b/lib/icinga/checkable-check.cpp
@@ -321,7 +321,7 @@ Checkable::ProcessingResult Checkable::ProcessCheckResult(const CheckResult::Ptr
 	olock.Unlock();
 
 	if (remove_acknowledgement_comments)
-		RemoveCommentsByType(CommentAcknowledgement);
+		RemoveAckComments(String(), cr->GetExecutionEnd());
 
 	Dictionary::Ptr vars_after = new Dictionary({
 		{ "state", new_state },
diff --git a/lib/icinga/checkable-comment.cpp b/lib/icinga/checkable-comment.cpp
index 135f35520..71cfac619 100644
--- a/lib/icinga/checkable-comment.cpp
+++ b/lib/icinga/checkable-comment.cpp
@@ -19,14 +19,19 @@ void Checkable::RemoveAllComments()
 	}
 }
 
-void Checkable::RemoveCommentsByType(int type, const String& removedBy)
+void Checkable::RemoveAckComments(const String& removedBy, double createdBefore)
 {
 	for (const Comment::Ptr& comment : GetComments()) {
-		/* Do not remove persistent comments from an acknowledgement */
-		if (comment->GetEntryType() == CommentAcknowledgement && comment->GetPersistent())
-			continue;
+		if (comment->GetEntryType() == CommentAcknowledgement) {
+			/* Do not remove persistent comments from an acknowledgement */
+			if (comment->GetPersistent()) {
+				continue;
+			}
+
+			if (comment->GetEntryTime() > createdBefore) {
+				continue;
+			}
 
-		if (comment->GetEntryType() == type) {
 			{
 				ObjectLock oLock (comment);
 				comment->SetRemovedBy(removedBy);
diff --git a/lib/icinga/checkable.hpp b/lib/icinga/checkable.hpp
index 6a46425a9..3d48b1445 100644
--- a/lib/icinga/checkable.hpp
+++ b/lib/icinga/checkable.hpp
@@ -17,6 +17,7 @@
 #include <condition_variable>
 #include <cstdint>
 #include <functional>
+#include <limits>
 
 namespace icinga
 {
@@ -156,7 +157,7 @@ public:
 
 	/* Comments */
 	void RemoveAllComments();
-	void RemoveCommentsByType(int type, const String& removedBy = String());
+	void RemoveAckComments(const String& removedBy = String(), double createdBefore = std::numeric_limits<double>::max());
 
 	std::set<Comment::Ptr> GetComments() const;
 	Comment::Ptr GetLastComment() const;
diff --git a/lib/icinga/externalcommandprocessor.cpp b/lib/icinga/externalcommandprocessor.cpp
index f781a3412..9850da030 100644
--- a/lib/icinga/externalcommandprocessor.cpp
+++ b/lib/icinga/externalcommandprocessor.cpp
@@ -665,7 +665,7 @@ void ExternalCommandProcessor::RemoveSvcAcknowledgement(double, const std::vecto
 		service->ClearAcknowledgement("");
 	}
 
-	service->RemoveCommentsByType(CommentAcknowledgement);
+	service->RemoveAckComments();
 }
 
 void ExternalCommandProcessor::AcknowledgeHostProblem(double, const std::vector<String>& arguments)
@@ -738,7 +738,7 @@ void ExternalCommandProcessor::RemoveHostAcknowledgement(double, const std::vect
 		ObjectLock olock(host);
 		host->ClearAcknowledgement("");
 	}
-	host->RemoveCommentsByType(CommentAcknowledgement);
+	host->RemoveAckComments();
 }
 
 void ExternalCommandProcessor::EnableHostgroupSvcChecks(double, const std::vector<String>& arguments)