.editorconfig

@@ -9,6 +9,7 @@ trim_trailing_whitespace = true
 charset = utf-8
 indent_style = space
 indent_size = 4
+tab_width = 4
 
 [*.{yml,yaml}]
 indent_size = 2

.gitignore

@@ -4,8 +4,6 @@ node_modules
 # Exclude macOS Finder (System Explorer) View States
 .DS_Store
 
-
-
 # Frontend build folders
 frontend/*/dist
 
@@ -19,3 +17,5 @@ sync-server/bindings/*.ts
 
 *.log
 *.sqlx
+
+target

frontend/obsidian-plugin/src/views/cursors/file-explorer.ts

@@ -34,7 +34,7 @@ export function renderCursorsInFileExplorer(
 			(parent) => {
 				cursors.forEach((cursor) => {
 					cursor.documentsWithCursors.forEach((document) => {
-						if (document.relative_path === key) {
+						if (document.relative_path.startsWith(key)) {
 							parent.appendChild(
 								createSpan({
 									text: cursor.userName,

frontend/obsidian-plugin/src/views/history/history-view.scss

@@ -4,6 +4,7 @@
 	background-color: var(--color-base-00);
 	border-radius: var(--radius-l);
 	container-type: inline-size;
+	word-break: break-word;
 
 	&.clickable {
 		cursor: pointer;
@@ -38,7 +39,6 @@
 			display: flex;
 			align-items: center;
 			gap: var(--size-4-2);
-			word-break: break-all;
 			margin: 0;
 
 			> span {

frontend/sync-client/src/sync-operations/unrestricted-syncer.ts

@@ -228,7 +228,8 @@ export class UnrestrictedSyncer {
 					},
 					message:
 						"File has been deleted remotely, so we deleted it locally",
-					author: response.userId
+					author: response.userId,
+					timestamp: new Date(response.updatedDate)
 				});
 
 				this.database.delete(document.relativePath);
@@ -325,7 +326,8 @@ export class UnrestrictedSyncer {
 					status: SyncStatus.SUCCESS,
 					details: actualUpdateDetails,
 					message: `Successfully downloaded remotely updated file from the server`,
-					author: response.userId
+					author: response.userId,
+					timestamp: new Date(response.updatedDate)
 				});
 			}
 		});
@@ -429,7 +431,8 @@ export class UnrestrictedSyncer {
 				status: SyncStatus.SUCCESS,
 				details: updateDetails,
 				message: `Successfully downloaded remote file which hadn't existed locally`,
-				author: remoteVersion.userId
+				author: remoteVersion.userId,
+				timestamp: new Date(remoteVersion.updatedDate)
 			});
 		});
 	}

frontend/sync-client/src/tracing/sync-history.ts

@@ -39,6 +39,7 @@ export interface CommonHistoryEntry {
 	message: string;
 	details: SyncDetails;
 	author?: string;
+	timestamp?: Date;
 }
 
 export enum SyncType {
@@ -92,7 +93,7 @@ export class SyncHistory {
 	public addHistoryEntry(entry: CommonHistoryEntry): void {
 		const historyEntry = {
 			...entry,
-			timestamp: new Date()
+			timestamp: entry.timestamp ?? new Date()
 		};
 
 		const candidate = this.findSimilarRecentUpdateEntry(historyEntry);

scripts/check.sh

@@ -21,7 +21,7 @@ else
     cargo fmt --all -- --check
 fi
 
-cargo machete
+cargo machete --with-metadata
 
 echo "Running checks in frontend"
 cd ../frontend

sync-server/Cargo.lock

@@ -991,6 +991,22 @@ version = "1.0.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "df3b46402a9d5adb4c86a0cf463f42e19994e3ee891101b1841f30a545cb49a9"
 
+[[package]]
+name = "humantime"
+version = "2.3.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "135b12329e5e3ce057a9f972339ea52bc954fe1e9358ef27f95e89716fbc5424"
+
+[[package]]
+name = "humantime-serde"
+version = "1.1.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "57a3db5ea5923d99402c94e9feb261dc5ee9b4efa158b0315f788cf549cc200c"
+dependencies = [
+ "humantime",
+ "serde",
+]
+
 [[package]]
 name = "hyper"
 version = "1.5.1"
@@ -2314,6 +2330,7 @@ dependencies = [
  "clap",
  "clap-verbosity-flag",
  "futures",
+ "humantime-serde",
  "log",
  "rand 0.9.0",
  "reconcile-text",

sync-server/Cargo.toml

@@ -20,6 +20,7 @@ axum_typed_multipart = "0.11.0"
 tower-http = { version = "0.6.1", features = ["cors", "trace", "limit", "timeout"] }
 tracing = "0.1.41"
 tracing-subscriber = { version = "0.3.19", features = ["fmt", "env-filter"]}
+humantime-serde = "1.1.1"
 sqlx = { version = "0.8.6", features = ["sqlite", "runtime-tokio", "uuid", "chrono"] }
 chrono = { version = "0.4.41", features = ["serde"] }
 rand = "0.9.0"
@@ -87,3 +88,6 @@ similar_names = { level = "allow", priority = 1 }
 missing_docs_in_private_items = { level = "allow", priority = 1 }
 
 pedantic = { level = "warn", priority = 0 }
+
+[package.metadata.cargo-machete]
+ignored = ["humantime-serde"]  # only used in serde macro

sync-server/config-e2e.yml

@@ -24,3 +24,6 @@ users:
       type: allow_list
       allowed:
       - default
+logging:
+  log_directory: logs
+  log_rotation: 7days

sync-server/src/app_state.rs

@@ -2,14 +2,12 @@ pub mod cursors;
 pub mod database;
 pub mod websocket;
 
-use std::ffi::OsString;
-
 use anyhow::Result;
 use cursors::Cursors;
 use database::Database;
 use websocket::broadcasts::Broadcasts;
 
-use crate::{config::Config, consts::DEFAULT_CONFIG_PATH};
+use crate::config::Config;
 
 #[derive(Clone, Debug)]
 pub struct AppState {
@@ -20,11 +18,7 @@ pub struct AppState {
 }
 
 impl AppState {
-    pub async fn try_new(config_path: Option<OsString>) -> Result<Self> {
-        let config_path = config_path.unwrap_or_else(|| OsString::from(DEFAULT_CONFIG_PATH));
-        let path = std::path::PathBuf::from(config_path);
-
-        let config = Config::read_or_create(&path).await?;
+    pub async fn try_new(config: Config) -> Result<Self> {
         let broadcasts = Broadcasts::new(&config.server);
         let database = Database::try_new(&config.database, &broadcasts).await?;
         let cursors: Cursors = Cursors::new(&config.database, &broadcasts);

sync-server/src/config.rs

@@ -3,12 +3,14 @@ use std::path::Path;
 use anyhow::{Context as _, Result};
 use database_config::DatabaseConfig;
 use log::info;
+use logging_config::LoggingConfig;
 use serde::{Deserialize, Serialize};
 use server_config::ServerConfig;
 use tokio::fs;
 use user_config::UserConfig;
 
 pub mod database_config;
+pub mod logging_config;
 pub mod server_config;
 pub mod user_config;
 
@@ -20,6 +22,8 @@ pub struct Config {
     pub server: ServerConfig,
     #[serde(default)]
     pub users: UserConfig,
+    #[serde(default)]
+    pub logging: LoggingConfig,
 }
 
 impl Config {

sync-server/src/config/logging_config.rs

@@ -0,0 +1,34 @@
+use std::time::Duration;
+
+use log::debug;
+use serde::{Deserialize, Serialize};
+
+use crate::consts::{DEFAULT_LOG_DIRECTORY, DEFAULT_LOG_ROTATION_INTERVAL};
+
+#[derive(Debug, Deserialize, Serialize, Clone)]
+pub struct LoggingConfig {
+    #[serde(default = "default_log_directory")]
+    pub log_directory: String,
+
+    #[serde(default = "default_log_rotation", with = "humantime_serde")]
+    pub log_rotation: Duration,
+}
+
+impl Default for LoggingConfig {
+    fn default() -> Self {
+        Self {
+            log_directory: default_log_directory(),
+            log_rotation: default_log_rotation(),
+        }
+    }
+}
+
+fn default_log_directory() -> String {
+    debug!("Using default log directory: {DEFAULT_LOG_DIRECTORY}");
+    DEFAULT_LOG_DIRECTORY.to_owned()
+}
+
+fn default_log_rotation() -> Duration {
+    debug!("Using default log rotation: {DEFAULT_LOG_ROTATION_INTERVAL:?}");
+    DEFAULT_LOG_ROTATION_INTERVAL
+}

sync-server/src/consts.rs

@@ -11,3 +11,6 @@ pub const DEFAULT_PORT: u16 = 3000;
 pub const DEFAULT_MAX_BODY_SIZE_MB: usize = 4096;
 pub const DEFAULT_RESPONSE_TIMEOUT_SECONDS: u64 = 60;
 pub const DEFAULT_MAX_CLIENTS_PER_VAULT: usize = 256;
+
+pub const DEFAULT_LOG_DIRECTORY: &str = "logs";
+pub const DEFAULT_LOG_ROTATION_INTERVAL: Duration = Duration::from_secs(60 * 60 * 24); // 1 day

sync-server/src/errors.rs

@@ -55,6 +55,7 @@ pub struct SerializedError {
 
 impl Display for SerializedError {
     fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        write!(f, "{}: {}", self.error_type, self.message)?;
         if !self.causes.is_empty() {
             write!(f, "\nCauses:\n")?;
             for cause in &self.causes {

sync-server/src/main.rs

@@ -6,24 +6,45 @@ mod errors;
 mod server;
 mod utils;
 
-use std::process::ExitCode;
+use std::{ffi::OsString, path::PathBuf, process::ExitCode};
 
 use anyhow::{Context as _, Result};
 use clap::Parser;
 use cli::args::Args;
+use config::Config;
+use consts::DEFAULT_CONFIG_PATH;
 use errors::{SyncServerError, init_error};
 use log::info;
 use server::create_server;
-use tracing_subscriber::{EnvFilter, fmt::format, util::SubscriberInitExt};
+use tracing_subscriber::{EnvFilter, fmt::format, layer::SubscriberExt, util::SubscriberInitExt};
+use utils::rotating_file_writer::RotatingFileWriter;
 
 #[tokio::main]
 async fn main() -> ExitCode {
     let args = Args::parse();
 
-    let mut result = set_up_logging(&args);
+    let config_path = args
+        .config_path
+        .clone()
+        .unwrap_or_else(|| OsString::from(DEFAULT_CONFIG_PATH));
+    let path = PathBuf::from(config_path);
+
+    let config = match Config::read_or_create(&path)
+        .await
+        .context("Failed to start server")
+        .map_err(init_error)
+    {
+        Ok(config) => config,
+        Err(e) => {
+            eprintln!("{}", e.serialize());
+            return ExitCode::FAILURE;
+        }
+    };
+
+    let mut result = set_up_logging(&args, &config.logging);
 
     if result.is_ok() {
-        result = start_server(args).await;
+        result = start_server(config).await;
     }
 
     match result {
@@ -35,7 +56,10 @@ async fn main() -> ExitCode {
     }
 }
 
-fn set_up_logging(args: &Args) -> Result<(), SyncServerError> {
+fn set_up_logging(
+    args: &Args,
+    logging_config: &config::logging_config::LoggingConfig,
+) -> Result<(), SyncServerError> {
     let level_filter = match args.verbose.log_level_filter() {
         // We don't want to allow disabling all logging
         log::LevelFilter::Off | log::LevelFilter::Error => tracing::Level::ERROR,
@@ -55,17 +79,33 @@ fn set_up_logging(args: &Args) -> Result<(), SyncServerError> {
 
     let is_debug_mode = args.verbose.log_level_filter() >= log::LevelFilter::Debug;
 
-    tracing_subscriber::fmt()
+    let file_appender = RotatingFileWriter::new(
+        &logging_config.log_directory,
+        "vault-link",
+        logging_config.log_rotation,
+    )
+    .context("Failed to create rotating file writer")
+    .map_err(init_error)?;
+
+    let format = format()
+        .with_target(is_debug_mode)
+        .with_line_number(is_debug_mode)
+        .compact();
+
+    let stdout_layer = tracing_subscriber::fmt::layer()
         .with_ansi(use_colors)
-        .with_env_filter(env_filter)
-        .event_format(
-            format()
-                .without_time()
-                .with_target(is_debug_mode)
-                .with_line_number(is_debug_mode)
-                .compact(),
-        )
-        .finish()
+        .with_writer(std::io::stdout)
+        .event_format(format.clone());
+
+    let file_layer = tracing_subscriber::fmt::layer()
+        .with_ansi(false)
+        .with_writer(file_appender)
+        .event_format(format);
+
+    tracing_subscriber::registry()
+        .with(env_filter)
+        .with(stdout_layer)
+        .with(file_layer)
         .try_init()
         .context("Failed to initialise tracing")
         .map_err(init_error)?;
@@ -73,13 +113,13 @@ fn set_up_logging(args: &Args) -> Result<(), SyncServerError> {
     Ok(())
 }
 
-async fn start_server(args: Args) -> Result<(), SyncServerError> {
+async fn start_server(config: Config) -> Result<(), SyncServerError> {
     info!(
         "Starting VaultLink server version {}",
         env!("CARGO_PKG_VERSION")
     );
 
-    create_server(args.config_path)
+    create_server(config)
         .await
         .context("Failed to start server")
         .map_err(init_error)

sync-server/src/server.rs

@@ -13,7 +13,7 @@ mod responses;
 mod update_document;
 mod websocket;
 
-use std::{ffi::OsString, time::Duration};
+use std::time::Duration;
 
 use anyhow::{Context as _, Result, anyhow};
 use auth::auth_middleware;
@@ -42,12 +42,12 @@ use tracing::{Level, info_span};
 
 use crate::{
     app_state::AppState,
-    config::server_config::ServerConfig,
+    config::{Config, server_config::ServerConfig},
     errors::{client_error, not_found_error},
 };
 
-pub async fn create_server(config_path: Option<OsString>) -> Result<()> {
-    let app_state = AppState::try_new(config_path)
+pub async fn create_server(config: Config) -> Result<()> {
+    let app_state = AppState::try_new(config)
         .await
         .context("Failed to initialise app state")?;
 

sync-server/src/utils.rs

@@ -1,4 +1,5 @@
 pub mod dedup_paths;
 pub mod is_file_type_mergable;
 pub mod normalize;
+pub mod rotating_file_writer;
 pub mod sanitize_path;

sync-server/src/utils/rotating_file_writer.rs

@@ -0,0 +1,364 @@
+use std::{
+    fs::{self, OpenOptions},
+    io::{self, Write},
+    path::{Path, PathBuf},
+    sync::{Arc, Mutex},
+    time::{Duration, SystemTime, UNIX_EPOCH},
+};
+
+use chrono::{Local, NaiveDateTime};
+use tracing_subscriber::fmt::MakeWriter;
+
+#[derive(Clone)]
+pub struct RotatingFileWriter {
+    inner: Arc<Mutex<RotatingFileWriterInner>>,
+}
+
+struct RotatingFileWriterInner {
+    directory: PathBuf,
+    file_prefix: String,
+    rotation_duration: Duration,
+    current_file: Option<std::fs::File>,
+    next_rotation_time: SystemTime,
+}
+
+impl RotatingFileWriter {
+    pub fn new(
+        directory: impl AsRef<Path>,
+        file_prefix: &str,
+        rotation_duration: Duration,
+    ) -> io::Result<Self> {
+        let directory = directory.as_ref().to_path_buf();
+
+        fs::create_dir_all(&directory)?;
+
+        let next_rotation_time =
+            Self::calculate_next_rotation_time(&directory, file_prefix, rotation_duration);
+
+        let inner = RotatingFileWriterInner {
+            directory,
+            file_prefix: file_prefix.to_owned(),
+            rotation_duration,
+            current_file: None,
+            next_rotation_time,
+        };
+
+        Ok(Self {
+            inner: Arc::new(Mutex::new(inner)),
+        })
+    }
+
+    /// Parse timestamp from log filename and return as `SystemTime`
+    fn parse_log_timestamp(filename: &str, file_prefix: &str) -> Option<SystemTime> {
+        // Expected format: {prefix}.{timestamp}.log where timestamp is %Y-%m-%d_%H-%M-%S
+        let prefix_len = file_prefix.len() + 1; // +1 for the dot
+        let timestamp_str = filename.get(prefix_len..filename.len().checked_sub(4)?)?;
+
+        let dt = NaiveDateTime::parse_from_str(timestamp_str, "%Y-%m-%d_%H-%M-%S").ok()?;
+        let timestamp = dt.and_local_timezone(Local).single()?;
+        let secs: u64 = timestamp.timestamp().try_into().ok()?;
+
+        Some(UNIX_EPOCH + Duration::from_secs(secs))
+    }
+
+    fn find_latest_log_file(directory: &Path, file_prefix: &str) -> Option<String> {
+        fs::read_dir(directory)
+            .ok()?
+            .filter_map(Result::ok)
+            .filter_map(|entry| {
+                let filename = entry.file_name().into_string().ok()?;
+                let has_correct_prefix = filename.starts_with(file_prefix);
+                let has_log_extension = Path::new(&filename)
+                    .extension()
+                    .is_some_and(|ext| ext.eq_ignore_ascii_case("log"));
+
+                (has_correct_prefix && has_log_extension).then_some(filename)
+            })
+            .max()
+    }
+
+    fn calculate_next_rotation_time(
+        directory: &Path,
+        file_prefix: &str,
+        rotation_duration: Duration,
+    ) -> SystemTime {
+        Self::find_latest_log_file(directory, file_prefix)
+            .and_then(|filename| Self::parse_log_timestamp(&filename, file_prefix))
+            .map_or_else(SystemTime::now, |last_rotation| {
+                last_rotation + rotation_duration
+            })
+    }
+
+    fn should_rotate(inner: &RotatingFileWriterInner) -> bool {
+        SystemTime::now() >= inner.next_rotation_time
+    }
+
+    fn rotate(inner: &mut RotatingFileWriterInner) -> io::Result<()> {
+        let timestamp = Local::now().format("%Y-%m-%d_%H-%M-%S");
+        let filename = format!("{}.{}.log", inner.file_prefix, timestamp);
+        let filepath = inner.directory.join(filename);
+
+        let file = OpenOptions::new()
+            .create(true)
+            .append(true)
+            .open(&filepath)?;
+
+        inner.current_file = Some(file);
+        inner.next_rotation_time = SystemTime::now() + inner.rotation_duration;
+
+        Ok(())
+    }
+}
+
+impl Write for RotatingFileWriter {
+    fn write(&mut self, buf: &[u8]) -> io::Result<usize> {
+        let mut inner = self.inner.lock().unwrap();
+
+        if inner.current_file.is_none() || Self::should_rotate(&inner) {
+            Self::rotate(&mut inner)?;
+        }
+
+        if let Some(ref mut file) = inner.current_file {
+            file.write(buf)
+        } else {
+            Err(io::Error::other("Failed to open log file"))
+        }
+    }
+
+    fn flush(&mut self) -> io::Result<()> {
+        let mut inner = self.inner.lock().unwrap();
+        if let Some(ref mut file) = inner.current_file {
+            file.flush()
+        } else {
+            Ok(())
+        }
+    }
+}
+
+impl<'a> MakeWriter<'a> for RotatingFileWriter {
+    type Writer = Self;
+
+    fn make_writer(&'a self) -> Self::Writer {
+        self.clone()
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use std::thread;
+
+    #[test]
+    fn test_write_creates_log_file_and_directory() {
+        let temp_dir = std::env::temp_dir().join("test_write_creates_log_file_and_directory");
+
+        let mut writer =
+            RotatingFileWriter::new(&temp_dir, "test", Duration::from_secs(3600)).unwrap();
+        writer.write_all(b"test log message\n").unwrap();
+        writer.flush().unwrap();
+
+        // Check that a log file was created
+        let entries: Vec<_> = fs::read_dir(&temp_dir)
+            .unwrap()
+            .filter_map(Result::ok)
+            .filter(|e| e.path().extension().is_some_and(|ext| ext == "log"))
+            .collect();
+
+        assert!(temp_dir.exists());
+        assert_eq!(entries.len(), 1);
+
+        fs::remove_dir_all(&temp_dir).unwrap();
+    }
+
+    #[test]
+    fn test_rotation_after_duration() {
+        let temp_dir = std::env::temp_dir().join("test_rotation_after_duration");
+
+        // Use a very short rotation duration
+        // Note: We need to wait at least 1 second between rotations since
+        // filename timestamps only have second precision
+        let mut writer =
+            RotatingFileWriter::new(&temp_dir, "test", Duration::from_millis(500)).unwrap();
+
+        writer.write_all(b"first message\n").unwrap();
+        writer.flush().unwrap();
+
+        // Wait for rotation time to pass (at least 1 second for different timestamp)
+        thread::sleep(Duration::from_millis(1100));
+
+        writer.write_all(b"second message\n").unwrap();
+        writer.flush().unwrap();
+
+        // Check that two log files were created
+        let entries: Vec<_> = fs::read_dir(&temp_dir)
+            .unwrap()
+            .filter_map(Result::ok)
+            .filter(|e| e.path().extension().is_some_and(|ext| ext == "log"))
+            .collect();
+
+        assert_eq!(entries.len(), 2);
+
+        fs::remove_dir_all(&temp_dir).unwrap();
+    }
+
+    #[test]
+    fn test_calculate_next_rotation_time_no_existing_logs() {
+        let temp_dir =
+            std::env::temp_dir().join("test_calculate_next_rotation_time_no_existing_logs");
+
+        fs::create_dir_all(&temp_dir).unwrap();
+
+        let before = SystemTime::now();
+        let next_rotation = RotatingFileWriter::calculate_next_rotation_time(
+            &temp_dir,
+            "test",
+            Duration::from_secs(3600),
+        );
+        let after = SystemTime::now();
+
+        // Should return current time (within a small window)
+        assert!(next_rotation >= before && next_rotation <= after + Duration::from_secs(1));
+
+        fs::remove_dir_all(&temp_dir).unwrap();
+    }
+
+    #[test]
+    fn test_calculate_next_rotation_time_with_existing_log() {
+        let temp_dir =
+            std::env::temp_dir().join("test_calculate_next_rotation_time_with_existing_log");
+
+        fs::create_dir_all(&temp_dir).unwrap();
+
+        // Create a log file with a known timestamp
+        let timestamp_str = "2025-10-26_14-30-00";
+        let filename = format!("test.{timestamp_str}.log");
+        fs::write(temp_dir.join(&filename), b"test").unwrap();
+
+        let rotation_duration = Duration::from_secs(3600);
+        let next_rotation =
+            RotatingFileWriter::calculate_next_rotation_time(&temp_dir, "test", rotation_duration);
+
+        // Parse the expected time
+        let expected_dt =
+            NaiveDateTime::parse_from_str(timestamp_str, "%Y-%m-%d_%H-%M-%S").unwrap();
+        let expected_timestamp = expected_dt.and_local_timezone(Local).single().unwrap();
+        let expected_duration =
+            Duration::from_secs(expected_timestamp.timestamp().try_into().unwrap());
+        let expected_next = UNIX_EPOCH + expected_duration + rotation_duration;
+
+        // Allow 1 second tolerance for timing differences
+        let diff = if next_rotation > expected_next {
+            next_rotation.duration_since(expected_next).unwrap()
+        } else {
+            expected_next.duration_since(next_rotation).unwrap()
+        };
+
+        assert!(
+            diff < Duration::from_secs(2),
+            "Expected {expected_next:?}, got {next_rotation:?}"
+        );
+
+        fs::remove_dir_all(&temp_dir).unwrap();
+    }
+
+    #[test]
+    fn test_picks_latest_log_file() {
+        let temp_dir = std::env::temp_dir().join("test_picks_latest_log_file");
+
+        fs::create_dir_all(&temp_dir).unwrap();
+
+        // Create multiple log files
+        fs::write(temp_dir.join("test.2025-10-26_10-00-00.log"), b"old").unwrap();
+        fs::write(temp_dir.join("test.2025-10-26_14-00-00.log"), b"newer").unwrap();
+        fs::write(temp_dir.join("test.2025-10-26_12-00-00.log"), b"middle").unwrap();
+
+        let rotation_duration = Duration::from_secs(3600);
+        let next_rotation =
+            RotatingFileWriter::calculate_next_rotation_time(&temp_dir, "test", rotation_duration);
+
+        // Should use the latest file (2025-10-26_14-00-00)
+        let expected_dt =
+            NaiveDateTime::parse_from_str("2025-10-26_14-00-00", "%Y-%m-%d_%H-%M-%S").unwrap();
+        let expected_timestamp = expected_dt.and_local_timezone(Local).single().unwrap();
+        let expected_duration =
+            Duration::from_secs(expected_timestamp.timestamp().try_into().unwrap());
+        let expected_next = UNIX_EPOCH + expected_duration + rotation_duration;
+
+        let diff = if next_rotation > expected_next {
+            next_rotation.duration_since(expected_next).unwrap()
+        } else {
+            expected_next.duration_since(next_rotation).unwrap()
+        };
+
+        assert!(diff < Duration::from_secs(2));
+
+        fs::remove_dir_all(&temp_dir).unwrap();
+    }
+
+    #[test]
+    fn test_ignores_malformed_filenames() {
+        let temp_dir = std::env::temp_dir().join("test_ignores_malformed_filenames");
+
+        fs::create_dir_all(&temp_dir).unwrap();
+
+        // Create log files with various malformed names
+        fs::write(temp_dir.join("test.invalid.log"), b"bad").unwrap();
+        fs::write(temp_dir.join("test.log"), b"bad2").unwrap();
+        fs::write(
+            temp_dir.join("other.2025-10-26_14-00-00.log"),
+            b"wrong prefix",
+        )
+        .unwrap();
+        fs::write(temp_dir.join("test.2025-10-26_14-00-00.txt"), b"wrong ext").unwrap();
+
+        let before = SystemTime::now();
+        let next_rotation = RotatingFileWriter::calculate_next_rotation_time(
+            &temp_dir,
+            "test",
+            Duration::from_secs(3600),
+        );
+        let after = SystemTime::now();
+
+        // Should fall back to current time since no valid logs exist
+        assert!(next_rotation >= before && next_rotation <= after + Duration::from_secs(1));
+
+        fs::remove_dir_all(&temp_dir).unwrap();
+    }
+
+    #[test]
+    fn test_restart_behavior() {
+        let temp_dir = std::env::temp_dir().join("test_restart_behavior");
+
+        // Create initial writer and write some data
+        {
+            let mut writer =
+                RotatingFileWriter::new(&temp_dir, "test", Duration::from_secs(3600)).unwrap();
+            writer.write_all(b"before restart\n").unwrap();
+            writer.flush().unwrap();
+        }
+
+        // Simulate restart by creating a new writer
+        thread::sleep(Duration::from_millis(100));
+        {
+            let mut writer =
+                RotatingFileWriter::new(&temp_dir, "test", Duration::from_secs(3600)).unwrap();
+            writer.write_all(b"after restart\n").unwrap();
+            writer.flush().unwrap();
+        }
+
+        // Should still have only one log file (no premature rotation)
+        let entries: Vec<_> = fs::read_dir(&temp_dir)
+            .unwrap()
+            .filter_map(Result::ok)
+            .filter(|e| e.path().extension().is_some_and(|ext| ext == "log"))
+            .collect();
+
+        assert_eq!(
+            entries.len(),
+            1,
+            "Should not create new log file on restart within rotation period"
+        );
+
+        fs::remove_dir_all(&temp_dir).unwrap();
+    }
+}