diff --git a/lib/services/access_request.go b/lib/services/access_request.go
index 2d5c407f05e..ba88ed32318 100644
--- a/lib/services/access_request.go
+++ b/lib/services/access_request.go
@@ -1393,17 +1393,14 @@ func (v *RequestValidator) isReasonRequired(ctx context.Context, requestedRoles
 func (m *RequestValidator) calculateMaxAccessDuration(req types.AccessRequest, sessionTTL time.Duration) (time.Duration, error) {
 	// Check if the maxDuration time is set.
 	maxDurationTime := req.GetMaxDuration()
-	if maxDurationTime.IsZero() {
-		return 0, nil
-	}
-
 	maxDuration := maxDurationTime.Sub(req.GetCreationTime())
 
 	// For dry run requests, use the maximum possible duration.
 	// This prevents the time drift that can occur as the value is set on the client side.
 	if req.GetDryRun() {
 		maxDuration = MaxAccessDuration
-	} else if maxDuration < 0 {
+		// maxDuration may end up < 0 even if maxDurationTime is set
+	} else if !maxDurationTime.IsZero() && maxDuration < 0 {
 		return 0, trace.BadParameter("invalid maxDuration: must be greater than creation time")
 	}
 
@@ -1411,26 +1408,19 @@ func (m *RequestValidator) calculateMaxAccessDuration(req types.AccessRequest, s
 		return 0, trace.BadParameter("max_duration must be less than or equal to %v", MaxAccessDuration)
 	}
 
-	minAdjDuration := maxDuration
+	var minAdjDuration time.Duration
 	// Adjust the expiration time if the max_duration value is set on the request role.
 	for _, roleName := range req.GetRoles() {
-		var maxDurationForRole time.Duration
-		for _, tms := range m.MaxDurationMatchers {
-			for _, matcher := range tms.Matchers {
-				if matcher.Match(roleName) {
-					if tms.MaxDuration > maxDurationForRole {
-						maxDurationForRole = tms.MaxDuration
-					}
-				}
-			}
-		}
-
-		if maxDurationForRole < minAdjDuration {
+		maxDurationForRole := m.maxDurationForRole(roleName)
+		if minAdjDuration == 0 || maxDurationForRole < minAdjDuration {
 			minAdjDuration = maxDurationForRole
 		}
 	}
+	if !maxDurationTime.IsZero() && maxDuration < minAdjDuration {
+		minAdjDuration = maxDuration
+	}
 
-	// minAdjDuration can end up being 0, if any role does not have
+	// minAdjDuration can end up being 0, if no role has a
 	// field `max_duration` defined.
 	// In this case, return the smaller value between the sessionTTL
 	// and the requested max duration.
@@ -1441,6 +1431,20 @@ func (m *RequestValidator) calculateMaxAccessDuration(req types.AccessRequest, s
 	return minAdjDuration, nil
 }
 
+func (m *RequestValidator) maxDurationForRole(roleName string) time.Duration {
+	var maxDurationForRole time.Duration
+	for _, tms := range m.MaxDurationMatchers {
+		for _, matcher := range tms.Matchers {
+			if matcher.Match(roleName) {
+				if tms.MaxDuration > maxDurationForRole {
+					maxDurationForRole = tms.MaxDuration
+				}
+			}
+		}
+	}
+	return maxDurationForRole
+}
+
 // calculatePendingRequestTTL calculates the TTL of the Access Request (how long it will await
 // approval). request TTL is capped to the smaller value between the const requestTTL and the
 // access request access expiry.
diff --git a/lib/services/access_request_test.go b/lib/services/access_request_test.go
index ea819059e5e..3e5cd903861 100644
--- a/lib/services/access_request_test.go
+++ b/lib/services/access_request_test.go
@@ -2673,6 +2673,14 @@ func TestValidate_RequestedMaxDuration(t *testing.T) {
 				},
 			},
 		},
+		"shortMaxDurationReqRole3": {
+			condition: types.RoleConditions{
+				Request: &types.AccessRequestConditions{
+					Roles:       []string{"requestedRole"},
+					MaxDuration: types.Duration(day),
+				},
+			},
+		},
 	}
 
 	// describes a collection of users with various roles
@@ -2681,6 +2689,7 @@ func TestValidate_RequestedMaxDuration(t *testing.T) {
 		"bob":   {"defaultRole"},
 		"carol": {"shortMaxDurationReqRole", "shortMaxDurationReqRole2"},
 		"david": {"maxDurationReqRole"},
+		"erin":  {"shortMaxDurationReqRole", "shortMaxDurationReqRole3", "maxDurationReqRole"},
 	}
 
 	defaultSessionTTL := 8 * time.Hour
@@ -2724,14 +2733,6 @@ func TestValidate_RequestedMaxDuration(t *testing.T) {
 			expectedSessionTTL:     8 * time.Hour,
 			dryRun:                 true,
 		},
-		{
-			desc:                   "role max_duration is ignored when requestedMaxDuration is not set",
-			requestor:              "alice",
-			roles:                  []string{"requestedRole"}, // role max_duration capped to 3 days
-			expectedAccessDuration: 8 * time.Hour,             // caps to defaultSessionTTL since requestedMaxDuration was not set
-			expectedPendingTTL:     8 * time.Hour,
-			expectedSessionTTL:     8 * time.Hour,
-		},
 		{
 			desc:                   "when role max_duration is not set: default to defaultSessionTTL when requestedMaxDuration is not set",
 			requestor:              "bob",
@@ -2812,6 +2813,25 @@ func TestValidate_RequestedMaxDuration(t *testing.T) {
 			expectedPendingTTL:     day,
 			expectedSessionTTL:     8 * time.Hour,
 		},
+		{
+			desc:                   "role max_duration is respected when requestedMaxDuration is not set",
+			requestor:              "alice",                   // has shortMaxDurationReqRole role assigned
+			roles:                  []string{"requestedRole"}, // caps max_duration to 3 days
+			expectedAccessDuration: 3 * day,
+			expectedPendingTTL:     3 * day,
+			expectedSessionTTL:     8 * time.Hour,
+		},
+		{
+			desc: "multiple roles with different max durations assigned",
+			// erin has the maxDurationReqRole (7 days) role assigned
+			// along with 2 other roles with shorter durations
+			// shortMaxDurationReqRole (3 days) and shortMaxDurationReqRole3 (1 day)
+			requestor:              "erin",
+			roles:                  []string{"requestedRole"}, // caps max_duration to 7 days
+			expectedAccessDuration: 7 * day,
+			expectedPendingTTL:     7 * day,
+			expectedSessionTTL:     8 * time.Hour,
+		},
 	}
 
 	for _, tt := range tts {
@@ -2832,7 +2852,9 @@ func TestValidate_RequestedMaxDuration(t *testing.T) {
 			require.NoError(t, err)
 
 			req.SetCreationTime(now)
-			req.SetMaxDuration(now.Add(tt.requestedMaxDuration))
+			if tt.requestedMaxDuration != 0 {
+				req.SetMaxDuration(now.Add(tt.requestedMaxDuration))
+			}
 			req.SetDryRun(tt.dryRun)
 
 			require.NoError(t, validator.Validate(context.Background(), req, identity))