diff --git a/cli/args/mod.rs b/cli/args/mod.rs
index bc384a132b..706d98852b 100644
--- a/cli/args/mod.rs
+++ b/cli/args/mod.rs
@@ -857,13 +857,17 @@ impl CliOptions {
       };
 
     if let Some(env_file_name) = &flags.env_file {
-      if (from_filename(env_file_name)).is_err() {
-        log::info!(
-          "{} The `--env` flag was used, but the dotenv file '{}' was not found.",
-          colors::yellow("Warning"),
-          env_file_name
-        );
-      }
+      match from_filename(env_file_name) {
+          Ok(_) => (),
+          Err(error) => {
+            match error {
+              dotenvy::Error::LineParse(line, index)=> log::info!("{} Parsing failed within the specified environment file: {} at index: {} of the value: {}",colors::yellow("Warning"), env_file_name, index, line),
+              dotenvy::Error::Io(_)=> log::info!("{} The `--env` flag was used, but the environment file specified '{}' was not found.",colors::yellow("Warning"),env_file_name),
+              dotenvy::Error::EnvVar(_)=>log::info!("{} One or more of the environment variables isn't present or not unicode within the specified environment file: {}",colors::yellow("Warning"),env_file_name),
+              _ => log::info!("{} Unknown failure occurred with the specified environment file: {}", colors::yellow("Warning"), env_file_name),
+            }
+          }
+        }
     }
 
     let disable_deprecated_api_warning = flags.log_level
diff --git a/tests/specs/eval/env_unparsable_file/__test__.jsonc b/tests/specs/eval/env_unparsable_file/__test__.jsonc
new file mode 100644
index 0000000000..cf5e9a99b2
--- /dev/null
+++ b/tests/specs/eval/env_unparsable_file/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "eval --env=../../../testdata/env_unparsable console.log(Deno.env.get(\"Another_FOO\"))",
+  "output": "main.out"
+}
diff --git a/tests/specs/eval/env_unparsable_file/main.out b/tests/specs/eval/env_unparsable_file/main.out
new file mode 100644
index 0000000000..18d7856b45
--- /dev/null
+++ b/tests/specs/eval/env_unparsable_file/main.out
@@ -0,0 +1,2 @@
+Warning Parsing failed within the specified environment file: ../../../testdata/env_unparsable at index: 3 of the value: c:\path
+undefined
diff --git a/tests/specs/run/env_unparsable_file/__test__.jsonc b/tests/specs/run/env_unparsable_file/__test__.jsonc
new file mode 100644
index 0000000000..bed1506356
--- /dev/null
+++ b/tests/specs/run/env_unparsable_file/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --env=../../../testdata/env_unparsable --allow-env main.js",
+  "output": "main.out"
+}
diff --git a/tests/specs/run/env_unparsable_file/main.js b/tests/specs/run/env_unparsable_file/main.js
new file mode 100644
index 0000000000..48488ce721
--- /dev/null
+++ b/tests/specs/run/env_unparsable_file/main.js
@@ -0,0 +1,3 @@
+console.log(Deno.env.get("FOO"));
+console.log(Deno.env.get("ANOTHER_FOO"));
+console.log(Deno.env.get("MULTILINE"));
diff --git a/tests/specs/run/env_unparsable_file/main.out b/tests/specs/run/env_unparsable_file/main.out
new file mode 100644
index 0000000000..a19ff4dd6c
--- /dev/null
+++ b/tests/specs/run/env_unparsable_file/main.out
@@ -0,0 +1,4 @@
+Warning Parsing failed within the specified environment file: ../../../testdata/env_unparsable at index: 3 of the value: c:\path
+valid
+undefined
+undefined
diff --git a/tests/testdata/env_unparsable b/tests/testdata/env_unparsable
new file mode 100644
index 0000000000..5542b80bc3
--- /dev/null
+++ b/tests/testdata/env_unparsable
@@ -0,0 +1,4 @@
+FOO=valid
+ANOTHER_FOO=c:\path
+MULTILINE="First Line
+Second Line"
\ No newline at end of file
diff --git a/tests/testdata/eval/env_file_missing.out b/tests/testdata/eval/env_file_missing.out
index 221acab934..2ec371438a 100644
--- a/tests/testdata/eval/env_file_missing.out
+++ b/tests/testdata/eval/env_file_missing.out
@@ -1,2 +1,2 @@
-Warning The `--env` flag was used, but the dotenv file 'missing' was not found.
+Warning The `--env` flag was used, but the environment file specified 'missing' was not found.
 undefined
diff --git a/tests/testdata/run/env_file_missing.out b/tests/testdata/run/env_file_missing.out
index ae1f8f595d..6ec9b298fc 100644
--- a/tests/testdata/run/env_file_missing.out
+++ b/tests/testdata/run/env_file_missing.out
@@ -1,4 +1,4 @@
-Warning The `--env` flag was used, but the dotenv file 'missing' was not found.
+Warning The `--env` flag was used, but the environment file specified 'missing' was not found.
 undefined
 undefined
 undefined