diff --git a/src/client_server/membership.rs b/src/client_server/membership.rs
index f99ff56a67b5f91cfdab57c4da716725a78d3446..5d028d9c071f9f2e06d0fee05e0c7f6dd329aff9 100644
--- a/src/client_server/membership.rs
+++ b/src/client_server/membership.rs
@@ -561,10 +561,10 @@ async fn join_room_by_id_helper(
             .chain(iter::once(Ok((event_id, join_event)))) // Add join event we just created
             .map(|r| {
                 let (event_id, value) = r?;
-                serde_json::from_value::<StateEvent>(value)
+                serde_json::from_value::<StateEvent>(value.clone())
                     .map(|ev| (event_id, Arc::new(ev)))
                     .map_err(|e| {
-                        warn!("{}", e);
+                        warn!("{}: {}", value, e);
                         Error::BadServerResponse("Invalid PDU bytes in send_join response.")
                     })
             })
diff --git a/src/database/media.rs b/src/database/media.rs
index 869d5d8077ba39d29d1ef8ad1fe9881d353cdc07..3ecf4bd9e03140db568274f2047c0b74664e4bfb 100644
--- a/src/database/media.rs
+++ b/src/database/media.rs
@@ -1,3 +1,5 @@
+use image::{imageops::FilterType, GenericImageView};
+
 use crate::{utils, Error, Result};
 use std::mem;
 
@@ -99,8 +101,34 @@ pub fn get(&self, mxc: &str) -> Result<Option<FileMeta>> {
         }
     }
 
+    /// Returns width, height of the thumbnail and whether it should be cropped. Returns None when
+    /// the server should send the original file.
+    pub fn thumbnail_properties(&self, width: u32, height: u32) -> Option<(u32, u32, bool)> {
+        match (width, height) {
+            (0..=32, 0..=32) => Some((32, 32, true)),
+            (0..=96, 0..=96) => Some((96, 96, true)),
+            (0..=320, 0..=240) => Some((320, 240, false)),
+            (0..=640, 0..=480) => Some((640, 480, false)),
+            (0..=800, 0..=600) => Some((800, 600, false)),
+            _ => None,
+        }
+    }
+
     /// Downloads a file's thumbnail.
+    ///
+    /// Here's an example on how it works:
+    ///
+    /// - Client requests an image with width=567, height=567
+    /// - Server rounds that up to (800, 600), so it doesn't have to save too many thumbnails
+    /// - Server rounds that up again to (958, 600) to fix the aspect ratio (only for width,height>96)
+    /// - Server creates the thumbnail and sends it to the user
+    ///
+    /// For width,height <= 96 the server uses another thumbnailing algorithm which crops the image afterwards.
     pub fn get_thumbnail(&self, mxc: String, width: u32, height: u32) -> Result<Option<FileMeta>> {
+        let (width, height, crop) = self
+            .thumbnail_properties(width, height)
+            .unwrap_or((0, 0, false)); // 0, 0 because that's the original file
+
         let mut main_prefix = mxc.as_bytes().to_vec();
         main_prefix.push(0xff);
 
@@ -146,6 +174,7 @@ pub fn get_thumbnail(&self, mxc: String, width: u32, height: u32) -> Result<Opti
             }))
         } else if let Some(r) = self.mediaid_file.scan_prefix(&original_prefix).next() {
             // Generate a thumbnail
+
             let (key, file) = r?;
             let mut parts = key.rsplit(|&b| b == 0xff);
 
@@ -169,7 +198,55 @@ pub fn get_thumbnail(&self, mxc: String, width: u32, height: u32) -> Result<Opti
             };
 
             if let Ok(image) = image::load_from_memory(&file) {
-                let thumbnail = image.thumbnail(width, height);
+                let original_width = image.width();
+                let original_height = image.height();
+                if width > original_width || height > original_height {
+                    return Ok(Some(FileMeta {
+                        filename,
+                        content_type,
+                        file: file.to_vec(),
+                    }));
+                }
+
+                let thumbnail = if crop {
+                    image.resize_to_fill(width, height, FilterType::Triangle)
+                } else {
+                    let (exact_width, exact_height) = {
+                        // Copied from image::dynimage::resize_dimensions
+                        let ratio = u64::from(original_width) * u64::from(height);
+                        let nratio = u64::from(width) * u64::from(original_height);
+
+                        let use_width = nratio > ratio;
+                        let intermediate = if use_width {
+                            u64::from(original_height) * u64::from(width) / u64::from(width)
+                        } else {
+                            u64::from(original_width) * u64::from(height)
+                                / u64::from(original_height)
+                        };
+                        if use_width {
+                            if intermediate <= u64::from(::std::u32::MAX) {
+                                (width, intermediate as u32)
+                            } else {
+                                (
+                                    (u64::from(width) * u64::from(::std::u32::MAX) / intermediate)
+                                        as u32,
+                                    ::std::u32::MAX,
+                                )
+                            }
+                        } else if intermediate <= u64::from(::std::u32::MAX) {
+                            (intermediate as u32, height)
+                        } else {
+                            (
+                                ::std::u32::MAX,
+                                (u64::from(height) * u64::from(::std::u32::MAX) / intermediate)
+                                    as u32,
+                            )
+                        }
+                    };
+
+                    image.thumbnail_exact(exact_width, exact_height)
+                };
+
                 let mut thumbnail_bytes = Vec::new();
                 thumbnail.write_to(&mut thumbnail_bytes, image::ImageOutputFormat::Png)?;
 
diff --git a/src/server_server.rs b/src/server_server.rs
index 3fefbd50943239a9ece0a9a5c0134c779c00544b..184f33390690a00aca137e49b07be93396804f7a 100644
--- a/src/server_server.rs
+++ b/src/server_server.rs
@@ -393,6 +393,7 @@ pub fn send_transaction_message_route<'a>(
             let mut pdu_id = pdu.room_id.as_bytes().to_vec();
             pdu_id.push(0xff);
             pdu_id.extend_from_slice(&count.to_be_bytes());
+            db.rooms.append_to_state(&pdu_id, &pdu)?;
             db.rooms.append_pdu(
                 &pdu,
                 &value,
@@ -402,7 +403,6 @@ pub fn send_transaction_message_route<'a>(
                 &db.account_data,
                 &db.sending,
             )?;
-            db.rooms.append_to_state(&pdu_id, &pdu)?;
         }
     }
     Ok(send_transaction_message::v1::Response {