diff --git a/docs/notes/2.26.x.md b/docs/notes/2.26.x.md
index 48835fc3540..e27429e070a 100644
--- a/docs/notes/2.26.x.md
+++ b/docs/notes/2.26.x.md
@@ -21,6 +21,7 @@ Thank you to [Klayvio](https://www.klaviyo.com/) and [Normal Computing](https://
 
 ### General
 
+- [Fixed](https://github.com/pantsbuild/pants/pull/21959) a bug where exponential backoff of file downloads could wait up to 18 days between retries under the default settings. [The `[GLOBAL].file_downloads_retry_delay ` option](https://www.pantsbuild.org/2.26/reference/global-options#file_downloads_retry_delay) is now used as a multiplier (previously it was the exponential base), and so any customisation of this option may need reconsideration for the new behaviour.
 
 ### Goals
 
diff --git a/src/rust/engine/Cargo.lock b/src/rust/engine/Cargo.lock
index 3bd889b2ce2..619f7301791 100644
--- a/src/rust/engine/Cargo.lock
+++ b/src/rust/engine/Cargo.lock
@@ -1161,7 +1161,7 @@ dependencies = [
  "testutil",
  "time",
  "tokio",
- "tokio-retry",
+ "tokio-retry2",
  "tokio-util 0.7.12",
  "tryfuture",
  "ui",
@@ -4286,13 +4286,12 @@ dependencies = [
 ]
 
 [[package]]
-name = "tokio-retry"
-version = "0.3.0"
+name = "tokio-retry2"
+version = "0.5.7"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7f57eb36ecbe0fc510036adff84824dd3c24bb781e21bfa67b69d556aa85214f"
+checksum = "1264d076dd34560544a2799e40e457bd07c43d30f4a845686b031bcd8455c84f"
 dependencies = [
  "pin-project",
- "rand",
  "tokio",
 ]
 
diff --git a/src/rust/engine/Cargo.toml b/src/rust/engine/Cargo.toml
index d6c9c08c390..7717b744abc 100644
--- a/src/rust/engine/Cargo.toml
+++ b/src/rust/engine/Cargo.toml
@@ -84,7 +84,7 @@ tempfile = { workspace = true }
 testutil_mock = { package = "mock", path = "testutil/mock" }
 time = { workspace = true }
 tokio = { workspace = true, features = ["macros", "rt", "rt-multi-thread"] }
-tokio-retry = { workspace = true }
+tokio-retry2 = { workspace = true }
 tokio-util = { workspace = true, features = ["io"] }
 tryfuture = { path = "tryfuture" }
 ui = { path = "ui" }
@@ -319,7 +319,7 @@ tempfile = "3.5.0"
 terminal_size = "0.1.15"
 time = "0.3.37"
 tokio = "1.32"
-tokio-retry = "0.3"
+tokio-retry2 = "0.5"
 tokio-rustls = "0.26"
 tokio-stream = "0.1"
 tokio-util = "0.7"
diff --git a/src/rust/engine/src/downloads.rs b/src/rust/engine/src/downloads.rs
index 28e8b5398af..60818cf297d 100644
--- a/src/rust/engine/src/downloads.rs
+++ b/src/rust/engine/src/downloads.rs
@@ -11,13 +11,13 @@ use std::time::Duration;
 use async_trait::async_trait;
 use bytes::{BufMut, Bytes};
 use futures::stream::StreamExt;
+use futures::TryFutureExt;
 use hashing::Digest;
 use humansize::{file_size_opts, FileSize};
 use reqwest::header::{HeaderMap, HeaderName};
 use reqwest::Error;
 use store::Store;
-use tokio_retry::strategy::{jitter, ExponentialBackoff};
-use tokio_retry::RetryIf;
+use tokio_retry2::{strategy::ExponentialFactorBackoff, Retry, RetryError};
 use url::Url;
 
 use workunit_store::{in_workunit, Level};
@@ -216,6 +216,10 @@ async fn attempt_download(
     Ok((digest, bytewriter.writer.into_inner().freeze()))
 }
 
+pub fn jitter(duration: Duration) -> Duration {
+    duration.mul_f64(rand::random::<f64>())
+}
+
 pub async fn download(
     http_client: &reqwest::Client,
     store: Store,
@@ -238,30 +242,30 @@ pub async fn download(
                 .unwrap()
         )),
         |_workunit| async move {
-            let retry_strategy = ExponentialBackoff::from_millis(error_delay.as_millis() as u64)
-                .map(jitter)
-                .take(max_attempts.get() - 1);
-            RetryIf::spawn(
-                retry_strategy,
-                || {
-                    attempt_number += 1;
-                    log::debug!("Downloading {} (attempt #{})", &url, &attempt_number);
-
-                    attempt_download(
-                        http_client,
-                        &url,
-                        &auth_headers,
-                        file_name.clone(),
-                        expected_digest,
-                    )
-                },
-                |err: &StreamingError| {
-                    let is_retryable = matches!(err, StreamingError::Retryable(_));
+            let retry_strategy =
+                ExponentialFactorBackoff::from_millis(error_delay.as_millis() as u64, 2.0)
+                    .map(jitter)
+                    .take(max_attempts.get() - 1);
+
+            return Retry::spawn(retry_strategy, || {
+                attempt_number += 1;
+                log::debug!("Downloading {} (attempt #{})", &url, &attempt_number);
+                attempt_download(
+                    http_client,
+                    &url,
+                    &auth_headers,
+                    file_name.clone(),
+                    expected_digest,
+                )
+                .map_err(|err| {
                     log::debug!("Error while downloading {}: {}", &url, err);
-                    is_retryable
-                },
-            )
-            .await
+                    match err {
+                        StreamingError::Retryable(msg) => RetryError::transient(msg),
+                        StreamingError::Permanent(msg) => RetryError::permanent(msg),
+                    }
+                })
+            })
+            .await;
         }
     )
     .await?;