diff --git a/docs/admin_reference.md b/docs/admin_reference.md
index 1c9d4fb0..7f23aee2 100644
--- a/docs/admin_reference.md
+++ b/docs/admin_reference.md
@@ -1078,7 +1078,10 @@ Respecting homeservers put this file here for listing administration, moderation
 
 * `delete` — - Deletes a single media file from our database and on the filesystem via a single MXC URL or event ID (not redacted)
 * `delete-list` — - Deletes a codeblock list of MXC URLs from our database and on the filesystem. This will always ignore errors
-* `delete-past-remote-media` — - Deletes all remote (and optionally local) media created before or after [duration] time using filesystem metadata first created at date, or fallback to last modified date. This will always ignore errors by default
+* `delete-past-remote-media` — Deletes all remote (and optionally local) media created before/after
+[duration] ago, using filesystem metadata first created at date, or
+fallback to last modified date. This will always ignore errors by
+default.
 * `delete-all-from-user` — - Deletes all the local media from a local user on our server. This will always ignore errors by default
 * `delete-all-from-server` — - Deletes all remote media from the specified remote server. This will always ignore errors by default
 * `get-file-info` —
@@ -1110,13 +1113,25 @@ Respecting homeservers put this file here for listing administration, moderation
 
 ## `admin media delete-past-remote-media`
 
-- Deletes all remote (and optionally local) media created before or after [duration] time using filesystem metadata first created at date, or fallback to last modified date. This will always ignore errors by default
+Deletes all remote (and optionally local) media created before/after
+[duration] ago, using filesystem metadata first created at date, or
+fallback to last modified date. This will always ignore errors by
+default.
+
+* Examples:
+  * Delete all remote media older than a year:
+
+    `!admin media delete-past-remote-media -b 1y`
+
+  * Delete all remote and local media from 3 days ago, up until now:
+
+    `!admin media delete-past-remote-media -a 3d --yes-i-want-to-delete-local-media`
 
 **Usage:** `admin media delete-past-remote-media [OPTIONS] <DURATION>`
 
 ###### **Arguments:**
 
-* `<DURATION>` — - The relative time (e.g. 30s, 5m, 7d) within which to search
+* `<DURATION>` — - The relative time (e.g. 30s, 5m, 7d) from now within which to search
 
 ###### **Options:**
 
diff --git a/src/admin/media/commands.rs b/src/admin/media/commands.rs
index 7aed28db..ab857ccd 100644
--- a/src/admin/media/commands.rs
+++ b/src/admin/media/commands.rs
@@ -2,7 +2,8 @@ use std::time::Duration;
 
 use conduwuit::{
 	Err, Result, debug, debug_info, debug_warn, error, info, trace,
-	utils::time::parse_timepoint_ago, warn,
+	utils::time::{TimeDirection, parse_timepoint_ago},
+	warn,
 };
 use conduwuit_service::media::Dim;
 use ruma::{Mxc, OwnedEventId, OwnedMxcUri, OwnedServerName};
@@ -235,14 +236,19 @@ pub(super) async fn delete_past_remote_media(
 	}
 	assert!(!(before && after), "--before and --after should not be specified together");
 
-	let duration = parse_timepoint_ago(&duration)?;
+	let direction = if after {
+		TimeDirection::After
+	} else {
+		TimeDirection::Before
+	};
+
+	let time_boundary = parse_timepoint_ago(&duration)?;
 	let deleted_count = self
 		.services
 		.media
-		.delete_all_remote_media_at_after_time(
-			duration,
-			before,
-			after,
+		.delete_all_media_within_timeframe(
+			time_boundary,
+			direction,
 			yes_i_want_to_delete_local_media,
 		)
 		.await?;
diff --git a/src/admin/media/mod.rs b/src/admin/media/mod.rs
index 66d49959..07f570a5 100644
--- a/src/admin/media/mod.rs
+++ b/src/admin/media/mod.rs
@@ -27,12 +27,24 @@ pub enum MediaCommand {
 	///   filesystem. This will always ignore errors.
 	DeleteList,
 
-	/// - Deletes all remote (and optionally local) media created before or
-	///   after [duration] time using filesystem metadata first created at date,
-	///   or fallback to last modified date. This will always ignore errors by
-	///   default.
+	/// Deletes all remote (and optionally local) media created before/after
+	/// [duration] ago, using filesystem metadata first created at date, or
+	/// fallback to last modified date. This will always ignore errors by
+	/// default.
+	///
+	/// * Examples:
+	///   * Delete all remote media older than a year:
+	///
+	///     `!admin media delete-past-remote-media -b 1y`
+	///
+	///   * Delete all remote and local media from 3 days ago, up until now:
+	///
+	///     `!admin media delete-past-remote-media -a 3d
+	/// --yes-i-want-to-delete-local-media`
+	#[command(verbatim_doc_comment)]
 	DeletePastRemoteMedia {
-		/// - The relative time (e.g. 30s, 5m, 7d) within which to search
+		/// - The relative time (e.g. 30s, 5m, 7d) from now within which to
+		///   search
 		duration: String,
 
 		/// - Only delete media created before [duration] ago
diff --git a/src/core/utils/tests.rs b/src/core/utils/tests.rs
index 05a0655b..69fc1a3b 100644
--- a/src/core/utils/tests.rs
+++ b/src/core/utils/tests.rs
@@ -276,3 +276,22 @@ async fn set_intersection_sorted_stream2() {
 		.await;
 	assert!(r.eq(&["ccc", "ggg", "iii"]));
 }
+
+#[test]
+fn is_within_bounds() {
+	use std::time::{Duration, SystemTime};
+
+	use utils::time::{TimeDirection, is_within_bounds};
+
+	let now = SystemTime::now();
+	let yesterday = now - Duration::from_secs(86400);
+	assert!(is_within_bounds(yesterday, now, TimeDirection::Before));
+	assert!(!is_within_bounds(yesterday, now, TimeDirection::After));
+
+	let tomorrow = now + Duration::from_secs(86400);
+	assert!(is_within_bounds(tomorrow, now, TimeDirection::After));
+	assert!(!is_within_bounds(tomorrow, now, TimeDirection::Before));
+
+	assert!(is_within_bounds(now, now, TimeDirection::Before));
+	assert!(is_within_bounds(now, now, TimeDirection::After));
+}
diff --git a/src/core/utils/time.rs b/src/core/utils/time.rs
index 394e08cb..b8fad41d 100644
--- a/src/core/utils/time.rs
+++ b/src/core/utils/time.rs
@@ -126,3 +126,24 @@ pub enum Unit {
 	Micros(u128),
 	Nanos(u128),
 }
+
+#[derive(Eq, PartialEq, Clone, Copy, Debug)]
+pub enum TimeDirection {
+	Before,
+	After,
+}
+
+/// Checks if `item_time` is before or after `time_boundary`.
+/// If both times are the same, it will return true for both directions, as the
+/// matching is inclusive.
+#[must_use]
+pub fn is_within_bounds(
+	item_time: SystemTime,
+	time_boundary: SystemTime,
+	direction: TimeDirection,
+) -> bool {
+	match direction {
+		| TimeDirection::Before => item_time <= time_boundary,
+		| TimeDirection::After => item_time >= time_boundary,
+	}
+}
diff --git a/src/service/media/mod.rs b/src/service/media/mod.rs
index b52fd320..aea52cea 100644
--- a/src/service/media/mod.rs
+++ b/src/service/media/mod.rs
@@ -11,7 +11,10 @@ use async_trait::async_trait;
 use base64::{Engine as _, engine::general_purpose};
 use conduwuit::{
 	Err, Result, Server, debug, debug_error, debug_info, debug_warn, err, error, trace,
-	utils::{self, MutexMap},
+	utils::{
+		self, MutexMap,
+		time::{self, TimeDirection},
+	},
 	warn,
 };
 use ruma::{Mxc, OwnedMxcUri, UserId, http_headers::ContentDisposition};
@@ -226,13 +229,12 @@ impl Service {
 		Ok(mxcs)
 	}
 
-	/// Deletes all remote only media files in the given at or after
-	/// time/duration. Returns a usize with the amount of media files deleted.
-	pub async fn delete_all_remote_media_at_after_time(
+	/// Deletes all media files in the given time frame.
+	/// Returns a usize with the amount of media files deleted.
+	pub async fn delete_all_media_within_timeframe(
 		&self,
-		time: SystemTime,
-		before: bool,
-		after: bool,
+		time_boundary: SystemTime,
+		direction: TimeDirection,
 		yes_i_want_to_delete_local_media: bool,
 	) -> Result<usize> {
 		let all_keys = self.db.get_all_media_keys().await;
@@ -299,18 +301,14 @@ impl Service {
 
 			debug!("File created at: {file_created_at:?}");
 
-			if file_created_at >= time && before {
+			if time::is_within_bounds(file_created_at, time_boundary, direction) {
 				debug!(
-					"File is within (before) user duration, pushing to list of file paths and \
-					 keys to delete."
-				);
-				remote_mxcs.push(mxc.to_string());
-			} else if file_created_at <= time && after {
-				debug!(
-					"File is not within (after) user duration, pushing to list of file paths \
-					 and keys to delete."
+					"File is within bounds ({direction:?} {time_boundary:?}), pushing to list \
+					 of file paths and keys to delete.",
 				);
 				remote_mxcs.push(mxc.to_string());
+			} else {
+				debug!("File is outside bounds ({direction:?} {time_boundary:?}), ignoring.");
 			}
 		}
 
@@ -318,7 +316,7 @@ impl Service {
 			return Err!(Database("Did not found any eligible MXCs to delete."));
 		}
 
-		debug_info!("Deleting media now in the past {time:?}");
+		debug_info!("Deleting media now {direction:?} {time_boundary:?}");
 
 		let mut deletion_count: usize = 0;