diff --git a/src/d2m/actions/create-room.js b/src/d2m/actions/create-room.js
index a1d9940..6127628 100644
--- a/src/d2m/actions/create-room.js
+++ b/src/d2m/actions/create-room.js
@@ -401,6 +401,7 @@ async function _syncRoom(channelID, shouldActuallySync) {
 	console.log(`[room sync] to matrix: ${channel.name}`)
 
 	const {spaceID, channelKState} = await channelToKState(channel, guild, {api}) // calling this in both branches because we don't want to calculate this if not syncing
+	await ks.kstateUploadMxc(channelKState) // pre-upload icons before diffing
 
 	// sync channel state to room
 	const roomKState = await ks.roomToKState(roomID)
diff --git a/src/d2m/actions/create-space.js b/src/d2m/actions/create-space.js
index 1fb1911..89e0f08 100644
--- a/src/d2m/actions/create-space.js
+++ b/src/d2m/actions/create-space.js
@@ -124,6 +124,8 @@ async function _syncSpace(guild, shouldActuallySync) {
 	console.log(`[space sync] to matrix: ${guild.name}`)
 
 	const guildKState = await guildToKState(guild, privacy_level) // calling this in both branches because we don't want to calculate this if not syncing
+	ks.kstateStripConditionals(guildKState) // pre-upload icons before diffing
+	await ks.kstateUploadMxc(guildKState)
 
 	// sync guild state to space
 	const spaceKState = await ks.roomToKState(spaceID)
@@ -185,6 +187,8 @@ async function syncSpaceFully(guildID) {
 	console.log(`[space sync] to matrix: ${guild.name}`)
 
 	const guildKState = await guildToKState(guild, privacy_level)
+	ks.kstateStripConditionals(guildKState) // pre-upload icons before diffing
+	await ks.kstateUploadMxc(guildKState)
 
 	// sync guild state to space
 	const spaceKState = await ks.roomToKState(spaceID)