diff --git a/config.example.toml b/config.example.toml
index 551ebc54..e2bb6e3c 100644
--- a/config.example.toml
+++ b/config.example.toml
@@ -103,6 +103,13 @@
 # enable_pipupgrade = true                         ###disabled by default
 # pipupgrade_arguments = "-y -u --pip-path pip"    ###disabled by default
 
+# For the poetry step, by default, Topgrade skips its update if poetry is not 
+# installed with the official script. This configuration entry forces Topgrade 
+# to run the update in this case.
+#
+# (default: false)
+# poetry_force_self_update = true
+
 
 [composer]
 # self_update = true
diff --git a/src/config.rs b/src/config.rs
index 62e3dc02..deafae4f 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -229,6 +229,7 @@ pub struct Python {
     enable_pip_review_local: Option<bool>,
     enable_pipupgrade: Option<bool>,
     pipupgrade_arguments: Option<String>,
+    poetry_force_self_update: Option<bool>,
 }
 
 #[derive(Deserialize, Default, Debug, Merge)]
@@ -1627,6 +1628,13 @@ impl Config {
             .and_then(|python| python.enable_pip_review_local)
             .unwrap_or(false)
     }
+    pub fn poetry_force_self_update(&self) -> bool {
+        self.config_file
+            .python
+            .as_ref()
+            .and_then(|python| python.poetry_force_self_update)
+            .unwrap_or(false)
+    }
 
     pub fn display_time(&self) -> bool {
         self.config_file
diff --git a/src/steps/generic.rs b/src/steps/generic.rs
index c4e323dd..1d125583 100644
--- a/src/steps/generic.rs
+++ b/src/steps/generic.rs
@@ -1,5 +1,6 @@
 #![allow(unused_imports)]
 
+use std::ffi::OsStr;
 use std::path::PathBuf;
 use std::process::Command;
 use std::{env, path::Path};
@@ -1029,8 +1030,88 @@ pub fn run_lensfun_update_data(ctx: &ExecutionContext) -> Result<()> {
 
 pub fn run_poetry(ctx: &ExecutionContext) -> Result<()> {
     let poetry = require("poetry")?;
+
+    #[cfg(unix)]
+    fn get_interpreter(poetry: &PathBuf) -> Result<PathBuf> {
+        use std::os::unix::ffi::OsStrExt;
+
+        let script = fs::read(poetry)?;
+        if let Some(r) = script.iter().position(|&b| b == b'\n') {
+            let first_line = &script[..r];
+            if first_line.starts_with(b"#!") {
+                return Ok(OsStr::from_bytes(&first_line[2..]).into());
+            }
+        }
+
+        Err(eyre!("Could not find shebang"))
+    }
+    #[cfg(windows)]
+    fn get_interpreter(poetry: &PathBuf) -> Result<PathBuf> {
+        let data = fs::read(poetry)?;
+
+        // https://bitbucket.org/vinay.sajip/simple_launcher/src/master/compare_launchers.py
+
+        let pos = match data.windows(4).rposition(|b| b == b"PK\x05\x06") {
+            Some(i) => i,
+            None => return Err(eyre!("Not a ZIP archive")),
+        };
+
+        let cdr_size = match data.get(pos + 12..pos + 16) {
+            Some(b) => u32::from_le_bytes(b.try_into().unwrap()) as usize,
+            None => return Err(eyre!("Invalid CDR size")),
+        };
+        let cdr_offset = match data.get(pos + 16..pos + 20) {
+            Some(b) => u32::from_le_bytes(b.try_into().unwrap()) as usize,
+            None => return Err(eyre!("Invalid CDR offset")),
+        };
+        if pos < cdr_size + cdr_offset {
+            return Err(eyre!("Invalid ZIP archive"));
+        }
+        let arc_pos = pos - cdr_size - cdr_offset;
+        let shebang = match data[..arc_pos].windows(2).rposition(|b| b == b"#!") {
+            Some(l) => &data[l + 2..arc_pos - 1],
+            None => return Err(eyre!("Could not find shebang")),
+        };
+
+        // shebang line is utf8
+        Ok(std::str::from_utf8(shebang)?.into())
+    }
+
+    if ctx.config().poetry_force_self_update() {
+        debug!("forcing poetry self update");
+    } else {
+        let interpreter = match get_interpreter(&poetry) {
+            Ok(p) => p,
+            Err(e) => {
+                return Err(SkipStep(format!("Could not find interpreter for {}: {}", poetry.display(), e)).into())
+            }
+        };
+        debug!("poetry interpreter: {}", interpreter.display());
+
+        let check_official_install_script =
+        "import sys; from os import path; print('Y') if path.isfile(path.join(sys.prefix, 'poetry_env')) else print('N')";
+        let output = Command::new(&interpreter)
+            .args(["-c", check_official_install_script])
+            .output_checked_utf8()?;
+        let stdout = output.stdout.trim();
+        let official_install = match stdout {
+            "N" => false,
+            "Y" => true,
+            _ => unreachable!("unexpected output from `check_official_install_script`"),
+        };
+
+        debug!("poetry is official install: {}", official_install);
+
+        if !official_install {
+            return Err(SkipStep("Not installed with the official script".to_string()).into());
+        }
+    }
+
     print_separator("Poetry");
-    ctx.run_type().execute(poetry).args(["self", "update"]).status_checked()
+    ctx.run_type()
+        .execute(&poetry)
+        .args(["self", "update"])
+        .status_checked()
 }
 
 pub fn run_uv(ctx: &ExecutionContext) -> Result<()> {