diff --git a/crates/nu-cli/src/commands/str_/to_datetime.rs b/crates/nu-cli/src/commands/str_/to_datetime.rs
index 7814d83ed..8909ddccb 100644
--- a/crates/nu-cli/src/commands/str_/to_datetime.rs
+++ b/crates/nu-cli/src/commands/str_/to_datetime.rs
@@ -123,7 +123,13 @@ fn action(
 
             let out = match DateTime::parse_from_str(s, dt) {
                 Ok(d) => UntaggedValue::date(d),
-                Err(_) => UntaggedValue::string(s),
+                Err(reason) => {
+                    return Err(ShellError::labeled_error(
+                        "could not parse as datetime",
+                        reason.to_string(),
+                        tag.into().span,
+                    ))
+                }
             };
 
             Ok(out.into_value(tag))
@@ -166,4 +172,15 @@ mod tests {
             _ => panic!("Didn't convert to date"),
         }
     }
+
+    #[test]
+    fn communicates_parsing_error_given_an_invalid_datetimelike_string() {
+        let date_str = string("16.11.1984 8:00 am Oops0000");
+
+        let fmt_options = DatetimeFormat("%d.%m.%Y %H:%M %P %z".to_string());
+
+        let actual = action(&date_str, &fmt_options, Tag::unknown());
+
+        assert!(actual.is_err());
+    }
 }
diff --git a/crates/nu-cli/src/commands/str_/to_decimal.rs b/crates/nu-cli/src/commands/str_/to_decimal.rs
index 3e908d22c..e07d0e08d 100644
--- a/crates/nu-cli/src/commands/str_/to_decimal.rs
+++ b/crates/nu-cli/src/commands/str_/to_decimal.rs
@@ -101,7 +101,13 @@ fn action(input: &Value, tag: impl Into<Tag>) -> Result<Value, ShellError> {
             let other = s.trim();
             let out = match BigDecimal::from_str(other) {
                 Ok(v) => UntaggedValue::decimal(v),
-                Err(_) => UntaggedValue::string(s),
+                Err(reason) => {
+                    return Err(ShellError::labeled_error(
+                        "could not parse as decimal",
+                        reason.to_string(),
+                        tag.into().span,
+                    ))
+                }
             };
             Ok(out.into_value(tag))
         }
@@ -138,4 +144,13 @@ mod tests {
         let actual = action(&word, Tag::unknown()).unwrap();
         assert_eq!(actual, expected);
     }
+
+    #[test]
+    fn communicates_parsing_error_given_an_invalid_decimallike_string() {
+        let decimal_str = string("11.6anra");
+
+        let actual = action(&decimal_str, Tag::unknown());
+
+        assert!(actual.is_err());
+    }
 }
diff --git a/crates/nu-cli/src/commands/str_/to_integer.rs b/crates/nu-cli/src/commands/str_/to_integer.rs
index 41277401a..2e2a92a48 100644
--- a/crates/nu-cli/src/commands/str_/to_integer.rs
+++ b/crates/nu-cli/src/commands/str_/to_integer.rs
@@ -101,7 +101,13 @@ fn action(input: &Value, tag: impl Into<Tag>) -> Result<Value, ShellError> {
             let other = s.trim();
             let out = match BigInt::from_str(other) {
                 Ok(v) => UntaggedValue::int(v),
-                Err(_) => UntaggedValue::string(s),
+                Err(reason) => {
+                    return Err(ShellError::labeled_error(
+                        "could not parse as an integer",
+                        reason.to_string(),
+                        tag.into().span,
+                    ))
+                }
             };
             Ok(out.into_value(tag))
         }
@@ -137,4 +143,13 @@ mod tests {
         let actual = action(&word, Tag::unknown()).unwrap();
         assert_eq!(actual, expected);
     }
+
+    #[test]
+    fn communicates_parsing_error_given_an_invalid_integerlike_string() {
+        let integer_str = string("36anra");
+
+        let actual = action(&integer_str, Tag::unknown());
+
+        assert!(actual.is_err());
+    }
 }
diff --git a/crates/nu-cli/tests/commands/keep_until.rs b/crates/nu-cli/tests/commands/keep_until.rs
index 6dab4273d..bc09099ec 100644
--- a/crates/nu-cli/tests/commands/keep_until.rs
+++ b/crates/nu-cli/tests/commands/keep_until.rs
@@ -37,8 +37,9 @@ fn condition_is_met() {
                 | skip 2
                 | split column ','
                 | headers
-                | skip-while "Chickens Collction" != "Blue Chickens"
+                | skip-while "Chicken Collection" != "Blue Chickens"
                 | keep-until "Chicken Collection" == "Red Chickens"
+                | skip 1
                 | str to-int "31/04/2020"
                 | get "31/04/2020"
                 | math sum
diff --git a/crates/nu-cli/tests/commands/mod.rs b/crates/nu-cli/tests/commands/mod.rs
index 1cfc9ca42..4996f054f 100644
--- a/crates/nu-cli/tests/commands/mod.rs
+++ b/crates/nu-cli/tests/commands/mod.rs
@@ -44,6 +44,7 @@ mod save;
 mod select;
 mod semicolon;
 mod skip_until;
+mod skip_while;
 mod sort_by;
 mod split_by;
 mod split_column;
diff --git a/crates/nu-cli/tests/commands/skip_until.rs b/crates/nu-cli/tests/commands/skip_until.rs
index 1344f49d9..bd3da95a3 100644
--- a/crates/nu-cli/tests/commands/skip_until.rs
+++ b/crates/nu-cli/tests/commands/skip_until.rs
@@ -38,6 +38,7 @@ fn condition_is_met() {
                 | split column ','
                 | headers
                 | skip-until "Chicken Collection" == "Red Chickens"
+                | skip 1
                 | str to-int "31/04/2020"
                 | get "31/04/2020"
                 | math sum
diff --git a/crates/nu-cli/tests/commands/skip_while.rs b/crates/nu-cli/tests/commands/skip_while.rs
new file mode 100644
index 000000000..4e5d17f9c
--- /dev/null
+++ b/crates/nu-cli/tests/commands/skip_while.rs
@@ -0,0 +1,51 @@
+use nu_test_support::fs::Stub::FileWithContentToBeTrimmed;
+use nu_test_support::playground::Playground;
+use nu_test_support::{nu, pipeline};
+
+#[test]
+fn condition_is_met() {
+    Playground::setup("skip-while_test_1", |dirs, sandbox| {
+        sandbox.with_files(vec![FileWithContentToBeTrimmed(
+            "caballeros.txt",
+            r#"
+                CHICKEN SUMMARY                        report date: April 29th, 2020
+                --------------------------------------------------------------------
+                Chicken Collection,29/04/2020,30/04/2020,31/04/2020,
+                Yellow Chickens,,,
+                Andrés,0,0,1
+                Jonathan,0,0,1
+                Jason,0,0,1
+                Yehuda,0,0,1
+                Blue Chickens,,,
+                Andrés,0,0,1
+                Jonathan,0,0,1
+                Jason,0,0,1
+                Yehuda,0,0,2
+                Red Chickens,,,
+                Andrés,0,0,1
+                Jonathan,0,0,1
+                Jason,0,0,1
+                Yehuda,0,0,3
+            "#,
+        )]);
+
+        let actual = nu!(
+            cwd: dirs.test(), pipeline(
+            r#"
+                open --raw caballeros.txt
+                | lines
+                | skip 2
+                | split column ','
+                | headers
+                | skip-while "Chicken Collection" != "Red Chickens"
+                | skip 1
+                | str to-int "31/04/2020"
+                | get "31/04/2020"
+                | math sum
+                | echo $it
+                "#
+        ));
+
+        assert_eq!(actual.out, "6");
+    })
+}