diff --git a/modules/actions/workflows.go b/modules/actions/workflows.go
index a538b6e290..fa248fa834 100644
--- a/modules/actions/workflows.go
+++ b/modules/actions/workflows.go
@@ -362,7 +362,7 @@ func matchIssuesEvent(issuePayload *api.IssuePayload, evt *jobparser.Event) bool
 			// Actions with the same name:
 			// opened, edited, closed, reopened, assigned, unassigned, milestoned, demilestoned
 			// Actions need to be converted:
-			// label_updated -> labeled
+			// label_updated -> labeled (when adding) or unlabeled (when removing)
 			// label_cleared -> unlabeled
 			// Unsupported activity types:
 			// deleted, transferred, pinned, unpinned, locked, unlocked
@@ -370,7 +370,12 @@ func matchIssuesEvent(issuePayload *api.IssuePayload, evt *jobparser.Event) bool
 			action := issuePayload.Action
 			switch action {
 			case api.HookIssueLabelUpdated:
-				action = "labeled"
+				// Check if any labels were removed to determine if this should be "labeled" or "unlabeled"
+				if len(issuePayload.RemovedLabels) > 0 {
+					action = "unlabeled"
+				} else {
+					action = "labeled"
+				}
 			case api.HookIssueLabelCleared:
 				action = "unlabeled"
 			}
diff --git a/modules/actions/workflows_test.go b/modules/actions/workflows_test.go
index c8e1e553fe..4062cdd6c2 100644
--- a/modules/actions/workflows_test.go
+++ b/modules/actions/workflows_test.go
@@ -136,3 +136,98 @@ func TestDetectMatched(t *testing.T) {
 		})
 	}
 }
+
+func TestMatchIssuesEvent(t *testing.T) {
+	testCases := []struct {
+		desc      string
+		payload   *api.IssuePayload
+		yamlOn    string
+		expected  bool
+		eventType string
+	}{
+		{
+			desc: "Label deletion should trigger unlabeled event",
+			payload: &api.IssuePayload{
+				Action: api.HookIssueLabelUpdated,
+				Issue: &api.Issue{
+					Labels: []*api.Label{},
+				},
+				RemovedLabels: []*api.Label{
+					{ID: 123, Name: "deleted-label"},
+				},
+			},
+			yamlOn:    "on:\n  issues:\n    types: [unlabeled]",
+			expected:  true,
+			eventType: "unlabeled",
+		},
+		{
+			desc: "Label deletion with existing labels should trigger unlabeled event",
+			payload: &api.IssuePayload{
+				Action: api.HookIssueLabelUpdated,
+				Issue: &api.Issue{
+					Labels: []*api.Label{
+						{ID: 456, Name: "existing-label"},
+					},
+				},
+				RemovedLabels: []*api.Label{
+					{ID: 123, Name: "deleted-label"},
+				},
+			},
+			yamlOn:    "on:\n  issues:\n    types: [unlabeled]",
+			expected:  true,
+			eventType: "unlabeled",
+		},
+		{
+			desc: "Label addition should trigger labeled event",
+			payload: &api.IssuePayload{
+				Action: api.HookIssueLabelUpdated,
+				Issue: &api.Issue{
+					Labels: []*api.Label{
+						{ID: 123, Name: "new-label"},
+					},
+				},
+				RemovedLabels: []*api.Label{}, // Empty array, no labels removed
+			},
+			yamlOn:    "on:\n  issues:\n    types: [labeled]",
+			expected:  true,
+			eventType: "labeled",
+		},
+		{
+			desc: "Label clear should trigger unlabeled event",
+			payload: &api.IssuePayload{
+				Action: api.HookIssueLabelCleared,
+				Issue: &api.Issue{
+					Labels: []*api.Label{},
+				},
+			},
+			yamlOn:    "on:\n  issues:\n    types: [unlabeled]",
+			expected:  true,
+			eventType: "unlabeled",
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.desc, func(t *testing.T) {
+			evts, err := GetEventsFromContent([]byte(tc.yamlOn))
+			assert.NoError(t, err)
+			assert.Len(t, evts, 1)
+
+			// Test if the event matches as expected
+			assert.Equal(t, tc.expected, matchIssuesEvent(tc.payload, evts[0]))
+
+			// For extra validation, use a direct call to test the actual mapping
+			action := tc.payload.Action
+			switch action {
+			case api.HookIssueLabelUpdated:
+				if len(tc.payload.RemovedLabels) > 0 {
+					action = "unlabeled"
+				} else {
+					action = "labeled"
+				}
+			case api.HookIssueLabelCleared:
+				action = "unlabeled"
+			}
+			assert.Equal(t, tc.eventType, string(action), "Event type should match expected")
+		})
+	}
+}
diff --git a/modules/structs/hook.go b/modules/structs/hook.go
index aaa9fbc9d3..890a99c8fe 100644
--- a/modules/structs/hook.go
+++ b/modules/structs/hook.go
@@ -310,13 +310,14 @@ const (
 
 // IssuePayload represents the payload information that is sent along with an issue event.
 type IssuePayload struct {
-	Action     HookIssueAction `json:"action"`
-	Index      int64           `json:"number"`
-	Changes    *ChangesPayload `json:"changes,omitempty"`
-	Issue      *Issue          `json:"issue"`
-	Repository *Repository     `json:"repository"`
-	Sender     *User           `json:"sender"`
-	CommitID   string          `json:"commit_id"`
+	Action        HookIssueAction `json:"action"`
+	Index         int64           `json:"number"`
+	Changes       *ChangesPayload `json:"changes,omitempty"`
+	RemovedLabels []*Label        `json:"removed_labels"`
+	Issue         *Issue          `json:"issue"`
+	Repository    *Repository     `json:"repository"`
+	Sender        *User           `json:"sender"`
+	CommitID      string          `json:"commit_id"`
 }
 
 // JSONPayload encodes the IssuePayload to JSON, with an indentation of two spaces.