diff --git a/CHANGELOG.md b/CHANGELOG.md
index 21339d0..1e0a066 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,7 @@
 - Add `config parse-from-url` command for parsing configuration from a URL
 - Add ability to download attachments for comments
 - Increase default http timeout to 120s
+- Add `--resume-on-error` flag when creating annotations
 
 # v0.28.0
 - Add general fields to `create datasets`
diff --git a/cli/src/commands/create/annotations.rs b/cli/src/commands/create/annotations.rs
index 7672230..285dbb2 100644
--- a/cli/src/commands/create/annotations.rs
+++ b/cli/src/commands/create/annotations.rs
@@ -47,6 +47,10 @@ pub struct CreateAnnotationsArgs {
     #[structopt(long = "batch-size", default_value = "128")]
     /// Number of comments to batch in a single request.
     batch_size: usize,
+
+    #[structopt(long = "resume-on-error")]
+    /// Whether to attempt to resume processing on error
+    resume_on_error: bool,
 }
 
 pub fn create(client: &Client, args: &CreateAnnotationsArgs, pool: &mut Pool) -> Result<()> {
@@ -95,6 +99,7 @@ pub fn create(client: &Client, args: &CreateAnnotationsArgs, pool: &mut Pool) ->
                 args.use_moon_forms,
                 args.batch_size,
                 pool,
+                args.resume_on_error,
             )?;
             if let Some(mut progress) = progress {
                 progress.done();
@@ -117,6 +122,7 @@ pub fn create(client: &Client, args: &CreateAnnotationsArgs, pool: &mut Pool) ->
                 args.use_moon_forms,
                 args.batch_size,
                 pool,
+                args.resume_on_error,
             )?;
             statistics
         }
@@ -131,8 +137,10 @@ pub fn create(client: &Client, args: &CreateAnnotationsArgs, pool: &mut Pool) ->
 
 pub trait AnnotationStatistic {
     fn add_annotation(&self);
+    fn add_failed_annotation(&self);
 }
 
+#[allow(clippy::too_many_arguments)]
 pub fn upload_batch_of_annotations(
     annotations_to_upload: &mut Vec<NewAnnotation>,
     client: &Client,
@@ -141,6 +149,7 @@ pub fn upload_batch_of_annotations(
     dataset_name: &DatasetFullName,
     use_moon_forms: bool,
     pool: &mut Pool,
+    resume_on_error: bool,
 ) -> Result<()> {
     let (error_sender, error_receiver) = channel();
 
@@ -182,15 +191,21 @@ pub fn upload_batch_of_annotations(
 
                 if let Err(error) = result {
                     error_sender.send(error).expect("Could not send error");
+                    statistics.add_failed_annotation();
+                } else {
+                    statistics.add_annotation();
                 }
-
-                statistics.add_annotation();
             });
         })
     });
 
     if let Ok(error) = error_receiver.try_recv() {
-        Err(error)
+        if resume_on_error {
+            annotations_to_upload.clear();
+            Ok(())
+        } else {
+            Err(error)
+        }
     } else {
         annotations_to_upload.clear();
         Ok(())
@@ -207,6 +222,7 @@ fn upload_annotations_from_reader(
     use_moon_forms: bool,
     batch_size: usize,
     pool: &mut Pool,
+    resume_on_error: bool,
 ) -> Result<()> {
     let mut annotations_to_upload = Vec::new();
 
@@ -224,6 +240,7 @@ fn upload_annotations_from_reader(
                     dataset_name,
                     use_moon_forms,
                     pool,
+                    resume_on_error,
                 )?;
             }
         }
@@ -238,6 +255,7 @@ fn upload_annotations_from_reader(
             dataset_name,
             use_moon_forms,
             pool,
+            resume_on_error,
         )?;
     }
 
@@ -307,12 +325,16 @@ fn read_annotations_iter<'a>(
 pub struct Statistics {
     bytes_read: AtomicUsize,
     annotations: AtomicUsize,
+    failed_annotations: AtomicUsize,
 }
 
 impl AnnotationStatistic for Statistics {
     fn add_annotation(&self) {
         self.annotations.fetch_add(1, Ordering::SeqCst);
     }
+    fn add_failed_annotation(&self) {
+        self.failed_annotations.fetch_add(1, Ordering::SeqCst);
+    }
 }
 
 impl Statistics {
@@ -320,6 +342,7 @@ impl Statistics {
         Self {
             bytes_read: AtomicUsize::new(0),
             annotations: AtomicUsize::new(0),
+            failed_annotations: AtomicUsize::new(0),
         }
     }
 
@@ -337,14 +360,32 @@ impl Statistics {
     pub fn num_annotations(&self) -> usize {
         self.annotations.load(Ordering::SeqCst)
     }
+
+    #[inline]
+    pub fn num_failed_annotations(&self) -> usize {
+        self.failed_annotations.load(Ordering::SeqCst)
+    }
 }
 
 fn basic_statistics(statistics: &Statistics) -> (u64, String) {
     let bytes_read = statistics.bytes_read();
     let num_annotations = statistics.num_annotations();
+    let num_failed_annotations = statistics.num_failed_annotations();
+
+    let failed_annotations_string = if num_failed_annotations > 0 {
+        format!(" {num_failed_annotations} {}", "skipped".dimmed())
+    } else {
+        String::new()
+    };
+
     (
         bytes_read as u64,
-        format!("{} {}", num_annotations, "annotations".dimmed(),),
+        format!(
+            "{} {}{}",
+            num_annotations,
+            "annotations".dimmed(),
+            failed_annotations_string
+        ),
     )
 }
 
diff --git a/cli/src/commands/create/comments.rs b/cli/src/commands/create/comments.rs
index e28624f..e18a7c3 100644
--- a/cli/src/commands/create/comments.rs
+++ b/cli/src/commands/create/comments.rs
@@ -74,6 +74,10 @@ pub struct CreateCommentsArgs {
     #[structopt(short = "y", long = "yes")]
     /// Consent to ai unit charge. Suppresses confirmation prompt.
     yes: bool,
+
+    #[structopt(long = "resume-on-error")]
+    /// Whether to attempt to resume processing on error
+    resume_on_error: bool,
 }
 
 pub fn create(client: &Client, args: &CreateCommentsArgs, pool: &mut Pool) -> Result<()> {
@@ -152,6 +156,7 @@ pub fn create(client: &Client, args: &CreateCommentsArgs, pool: &mut Pool) -> Re
                 args.use_moon_forms,
                 args.no_charge,
                 pool,
+                args.resume_on_error,
             )?;
             if let Some(mut progress) = progress {
                 progress.done();
@@ -180,6 +185,7 @@ pub fn create(client: &Client, args: &CreateCommentsArgs, pool: &mut Pool) -> Re
                 args.use_moon_forms,
                 args.no_charge,
                 pool,
+                args.resume_on_error,
             )?;
             statistics
         }
@@ -330,6 +336,7 @@ fn upload_comments_from_reader(
     use_moon_forms: bool,
     no_charge: bool,
     pool: &mut Pool,
+    resume_on_error: bool,
 ) -> Result<()> {
     assert!(batch_size > 0);
 
@@ -415,6 +422,7 @@ fn upload_comments_from_reader(
                     dataset_name,
                     use_moon_forms,
                     pool,
+                    resume_on_error,
                 )?;
             }
         }
@@ -442,6 +450,7 @@ fn upload_comments_from_reader(
                 dataset_name,
                 use_moon_forms,
                 pool,
+                resume_on_error,
             )?;
         }
     }
@@ -464,12 +473,16 @@ pub struct Statistics {
     updated: AtomicUsize,
     unchanged: AtomicUsize,
     annotations: AtomicUsize,
+    failed_annotations: AtomicUsize,
 }
 
 impl AnnotationStatistic for Statistics {
     fn add_annotation(&self) {
         self.annotations.fetch_add(1, Ordering::SeqCst);
     }
+    fn add_failed_annotation(&self) {
+        self.failed_annotations.fetch_add(1, Ordering::SeqCst);
+    }
 }
 
 impl Statistics {
@@ -481,6 +494,7 @@ impl Statistics {
             updated: AtomicUsize::new(0),
             unchanged: AtomicUsize::new(0),
             annotations: AtomicUsize::new(0),
+            failed_annotations: AtomicUsize::new(0),
         }
     }
 
@@ -526,6 +540,11 @@ impl Statistics {
     fn num_annotations(&self) -> usize {
         self.annotations.load(Ordering::SeqCst)
     }
+
+    #[inline]
+    fn num_failed_annotations(&self) -> usize {
+        self.failed_annotations.load(Ordering::SeqCst)
+    }
 }
 
 /// Detailed statistics - only make sense if using --overwrite (i.e. exclusively sync endpoint)
@@ -537,10 +556,17 @@ fn detailed_statistics(statistics: &Statistics) -> (u64, String) {
     let num_updated = statistics.num_updated();
     let num_unchanged = statistics.num_unchanged();
     let num_annotations = statistics.num_annotations();
+    let num_failed_annotations = statistics.num_failed_annotations();
+    let failed_annotations_string = if num_failed_annotations > 0 {
+        format!(" {num_failed_annotations} {}", "skipped".dimmed())
+    } else {
+        String::new()
+    };
+
     (
         bytes_read as u64,
         format!(
-            "{} {}: {} {} {} {} {} {} [{} {}]",
+            "{} {}: {} {} {} {} {} {} [{} {}{}]",
             num_uploaded.to_string().bold(),
             "comments".dimmed(),
             num_new,
@@ -551,6 +577,7 @@ fn detailed_statistics(statistics: &Statistics) -> (u64, String) {
             "nop".dimmed(),
             num_annotations,
             "annotations".dimmed(),
+            failed_annotations_string
         ),
     )
 }
@@ -560,14 +587,22 @@ fn basic_statistics(statistics: &Statistics) -> (u64, String) {
     let bytes_read = statistics.bytes_read();
     let num_uploaded = statistics.num_uploaded();
     let num_annotations = statistics.num_annotations();
+    let num_failed_annotations = statistics.num_failed_annotations();
+    let failed_annotations_string = if num_failed_annotations > 0 {
+        format!(" {num_failed_annotations} {}", "skipped".dimmed())
+    } else {
+        String::new()
+    };
+
     (
         bytes_read as u64,
         format!(
-            "{} {} [{} {}]",
+            "{} {} [{} {}{}]",
             num_uploaded.to_string().bold(),
             "comments".dimmed(),
             num_annotations,
             "annotations".dimmed(),
+            failed_annotations_string
         ),
     )
 }