diff --git a/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/QQAndroidBot.kt b/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/QQAndroidBot.kt
index 687f4ef0b..f6b46ddbc 100644
--- a/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/QQAndroidBot.kt
+++ b/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/QQAndroidBot.kt
@@ -402,7 +402,12 @@ internal abstract class QQAndroidBotBase constructor(
             val resId: String
             when (response) {
                 is MultiMsg.ApplyUp.Response.MessageTooLarge ->
-                    error("message is too large")
+                    error(
+                        "Internal error: message is too large, but this should be handled before sending. Message content:" +
+                                message.joinToString {
+                                    "${it::class.simpleName}(l=${it.toString().length})"
+                                }
+                    )
                 is MultiMsg.ApplyUp.Response.RequireUpload -> {
                     resId = response.proto.msgResid
 
diff --git a/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/contact/GroupImpl.kt b/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/contact/GroupImpl.kt
index 43af7cae5..cd874bae5 100644
--- a/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/contact/GroupImpl.kt
+++ b/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/contact/GroupImpl.kt
@@ -30,7 +30,6 @@ import net.mamoe.mirai.qqandroid.network.highway.HighwayHelper
 import net.mamoe.mirai.qqandroid.network.protocol.packet.chat.TroopManagement
 import net.mamoe.mirai.qqandroid.network.protocol.packet.chat.image.ImgStore
 import net.mamoe.mirai.qqandroid.network.protocol.packet.chat.receive.MessageSvc
-import net.mamoe.mirai.qqandroid.utils.estimateLength
 import net.mamoe.mirai.qqandroid.utils.toIpV4AddressString
 import net.mamoe.mirai.utils.*
 import kotlin.contracts.ExperimentalContracts
@@ -285,7 +284,7 @@ internal class GroupImpl(
                 throw EventCancelledException("cancelled by GroupMessageSendEvent")
             }
 
-            val length = event.message.estimateLength(5001)
+            val length = event.message.toString().length
             if (!(length <= 5000 && event.message.count { it is Image } <= 50)) {
                 throw MessageTooLargeException(
                     this,
@@ -294,10 +293,17 @@ internal class GroupImpl(
                     "message(${event.message.joinToString(
                         "",
                         limit = 10
-                    )}) is too large. Allow up to 5000 in weight (Chinese char=4, English char=1, Quote=700, Image=800, others are estimated in String length.)"
+                    )}) is too large. Allow up to 50 images or 5000 chars"
                 )
             }
-            if (length >= 800) {
+
+            val imageCount = event.message.count { it is Image }
+
+            if (length >= 800
+                || imageCount >= 4
+                || (event.message.any<QuoteReply>()
+                        && (imageCount != 0 || length > 100))
+            ) {
                 return bot.lowLevelSendLongGroupMessage(this.id, event.message)
             }
 
diff --git a/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/network/protocol/packet/chat/MultiMsg.kt b/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/network/protocol/packet/chat/MultiMsg.kt
index 35f1daa37..4ef576578 100644
--- a/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/network/protocol/packet/chat/MultiMsg.kt
+++ b/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/network/protocol/packet/chat/MultiMsg.kt
@@ -49,7 +49,7 @@ internal fun MessageChain.calculateValidationDataForGroup(
     groupCode: Long,
     botMemberNameCard: String
 ): MessageValidationData {
-    val richTextElems = this.toRichTextElems(true, false)
+    val richTextElems = this.toRichTextElems(forGroup = true, withGeneralFlags = false)
 
     val msgTransmit = MsgTransmit.PbMultiMsgTransmit(
         msg = listOf(
diff --git a/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/utils/type.kt b/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/utils/type.kt
index 23df48254..854f69944 100644
--- a/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/utils/type.kt
+++ b/mirai-core-qqandroid/src/commonMain/kotlin/net/mamoe/mirai/qqandroid/utils/type.kt
@@ -33,7 +33,7 @@ internal fun Int.toIpV4AddressString(): String {
 }
 
 internal fun String.chineseLength(upTo: Int): Int {
-    return this.sumUpTo(upTo) { if (it in '\u0391'..'\uFFE5') 4 else 1 }
+    return this.sumUpTo(upTo) { if (it in '\u0391'..'\uFFE5') 3 else 1 }
 }
 
 internal fun MessageChain.estimateLength(upTo: Int = Int.MAX_VALUE): Int =
@@ -47,7 +47,7 @@ internal fun SingleMessage.estimateLength(upTo: Int = Int.MAX_VALUE): Int {
         is QuoteReply -> {
             700 + source.originalMessage.estimateLength(upTo)
         }
-        is Image -> 300
+        // is Image -> 300
         is PlainText -> stringValue.chineseLength(upTo)
         is At -> display.chineseLength(upTo)
         is AtAll -> display.chineseLength(upTo)