diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8d69ef8fb3..cfbdd645a0 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,13 @@
 
 "You know what they say. Fool me once, strike one, but fool me twice... strike three." — Michael Scott
 
+## Unreleased
+
+### Fixes
+
+- Don't use hidden progress bar ([#2830](https://github.com/getsentry/sentry-cli/pull/2830)) by @lcian
+  - Fixed an issue where log messages would not show up when redirecting stderr to a file and using any subcommand that uses a progress bar, such as `sentry-cli debug-files bundle-jvm` and `sentry-cli sourcemaps upload`.
+
 ## 2.56.1
 
 ### Deprecations
diff --git a/src/commands/debug_files/find.rs b/src/commands/debug_files/find.rs
index 4b63cf2517..f1e1fa907d 100644
--- a/src/commands/debug_files/find.rs
+++ b/src/commands/debug_files/find.rs
@@ -117,7 +117,7 @@ fn find_ids(
         .filter(|e| e.file_type().is_file());
 
     let mut found_files = vec![];
-    let pb = ProgressBar::new_spinner();
+    let mut pb = ProgressBar::new_spinner();
     pb.set_style(
         ProgressStyle::default_spinner()
             .tick_chars("/|\\- ")
@@ -136,7 +136,7 @@ fn find_ids(
             pb.set_message(p);
         }
         pb.tick();
-        pb.set_prefix(&format!("{}", found_files.len()));
+        pb.set_prefix(format!("{}", found_files.len()));
 
         let found: Vec<_> = types
             .iter()
diff --git a/src/utils/chunks/upload.rs b/src/utils/chunks/upload.rs
index a05c8425af..7425fe104f 100644
--- a/src/utils/chunks/upload.rs
+++ b/src/utils/chunks/upload.rs
@@ -182,7 +182,7 @@ where
     );
 
     let api = Api::current();
-    let pb = ProgressBar::new(chunked_objects.len());
+    let mut pb = ProgressBar::new(chunked_objects.len());
     pb.set_style(progress_style);
     pb.set_prefix(">");
 
diff --git a/src/utils/dif_upload/mod.rs b/src/utils/dif_upload/mod.rs
index 1b12e2d892..9f4b6a9344 100644
--- a/src/utils/dif_upload/mod.rs
+++ b/src/utils/dif_upload/mod.rs
@@ -636,7 +636,7 @@ fn search_difs(options: &DifUpload) -> Result<Vec<DifMatch<'static>>> {
          \n  found {prefix:.yellow} {msg:.dim}",
     );
 
-    let pb = ProgressBar::new_spinner();
+    let mut pb = ProgressBar::new_spinner();
     pb.enable_steady_tick(100);
     pb.set_style(progress_style);
 
@@ -668,7 +668,7 @@ fn search_difs(options: &DifUpload) -> Result<Vec<DifMatch<'static>>> {
                 }
             };
 
-            pb.set_prefix(&collected.len().to_string());
+            pb.set_prefix(collected.len().to_string());
             Ok(())
         })?;
     }
@@ -958,7 +958,7 @@ where
          \n{wide_bar}  {pos}/{len}",
     );
 
-    let pb = ProgressBar::new(items.len());
+    let mut pb = ProgressBar::new(items.len());
     pb.set_style(progress_style);
     pb.set_prefix(">");
 
@@ -1019,7 +1019,7 @@ fn process_symbol_maps<'a>(
          \n{wide_bar}  {pos}/{len}",
     );
 
-    let pb = ProgressBar::new(len);
+    let mut pb = ProgressBar::new(len);
     pb.set_style(progress_style);
     pb.set_prefix(">");
 
@@ -1110,7 +1110,7 @@ fn create_source_bundles<'a>(
          \n{wide_bar}  {pos}/{len}",
     );
 
-    let pb = ProgressBar::new(difs.len());
+    let mut pb = ProgressBar::new(difs.len());
     pb.set_style(progress_style);
     pb.set_prefix(">");
 
@@ -1166,7 +1166,7 @@ fn create_il2cpp_mappings<'a>(difs: &[DifMatch<'a>]) -> Result<Vec<DifMatch<'a>>
          \n{wide_bar}  {pos}/{len}",
     );
 
-    let pb = ProgressBar::new(difs.len());
+    let mut pb = ProgressBar::new(difs.len());
     pb.set_style(progress_style);
     pb.set_prefix(">");
 
diff --git a/src/utils/file_search.rs b/src/utils/file_search.rs
index 539f0400e1..1fdb50fb14 100644
--- a/src/utils/file_search.rs
+++ b/src/utils/file_search.rs
@@ -98,7 +98,7 @@ impl ReleaseFileSearch {
         \n  found {prefix:.yellow} {msg:.dim}",
         );
 
-        let pb = ProgressBar::new_spinner();
+        let mut pb = ProgressBar::new_spinner();
         pb.enable_steady_tick(100);
         pb.set_style(progress_style);
 
@@ -139,7 +139,7 @@ impl ReleaseFileSearch {
             if file.file_type().is_some_and(|t| t.is_dir()) {
                 continue;
             }
-            pb.set_message(&format!("{}", file.path().display()));
+            pb.set_message(format!("{}", file.path().display()));
 
             info!("found: {} ({} bytes)", file.path().display(), {
                 #[expect(clippy::unwrap_used, reason = "legacy code")]
@@ -164,7 +164,7 @@ impl ReleaseFileSearch {
             };
             collected.push(file_match);
 
-            pb.set_prefix(&collected.len().to_string());
+            pb.set_prefix(collected.len().to_string());
         }
 
         pb.finish_and_clear();
diff --git a/src/utils/file_upload.rs b/src/utils/file_upload.rs
index 15db8419a9..78714914a4 100644
--- a/src/utils/file_upload.rs
+++ b/src/utils/file_upload.rs
@@ -684,7 +684,7 @@ fn build_artifact_bundle(
        \n{wide_bar}  {pos}/{len}",
     );
 
-    let pb = ProgressBar::new(files.len());
+    let mut pb = ProgressBar::new(files.len());
     pb.set_style(progress_style);
     pb.set_prefix(">");
 
diff --git a/src/utils/progress.rs b/src/utils/progress.rs
index d0355c618f..cc912fd5b7 100644
--- a/src/utils/progress.rs
+++ b/src/utils/progress.rs
@@ -1,6 +1,6 @@
 use parking_lot::RwLock;
 use std::env;
-use std::ops::Deref;
+use std::io::IsTerminal as _;
 use std::sync::Arc;
 use std::time::Instant;
 
@@ -8,69 +8,134 @@ use crate::utils::logging;
 
 pub use indicatif::ProgressStyle;
 
-pub fn is_progress_bar_visible() -> bool {
-    env::var("SENTRY_NO_PROGRESS_BAR") != Ok("1".into())
+/// By default, use the progress bar when we can detect we're running in a terminal.
+/// `SENTRY_NO_PROGRESS_BAR` takes precedence and can be used to disable the progress bar
+/// regardless of whether or not we're in a terminal.
+pub fn use_progress_bar() -> bool {
+    if env::var("SENTRY_NO_PROGRESS_BAR") == Ok("1".into()) {
+        return false;
+    }
+    std::io::stderr().is_terminal()
 }
 
+/// Wrapper that optionally holds a progress bar.
+/// If there's a progress bar, forward calls to it.
+/// Otherwise, forward messages to `log` calls.
 pub struct ProgressBar {
-    inner: Arc<indicatif::ProgressBar>,
+    inner: Option<Arc<indicatif::ProgressBar>>,
     start: Instant,
+    prefix: Option<String>,
 }
 
 impl ProgressBar {
     pub fn new(len: usize) -> Self {
-        if is_progress_bar_visible() {
-            indicatif::ProgressBar::new(len as u64).into()
+        if use_progress_bar() {
+            Self::from_indicatif(indicatif::ProgressBar::new(len as u64))
         } else {
-            Self::hidden()
+            Self::no_progress_bar()
         }
     }
 
     pub fn new_spinner() -> Self {
-        if is_progress_bar_visible() {
-            indicatif::ProgressBar::new_spinner().into()
+        if use_progress_bar() {
+            Self::from_indicatif(indicatif::ProgressBar::new_spinner())
         } else {
-            Self::hidden()
+            Self::no_progress_bar()
         }
     }
 
-    pub fn hidden() -> Self {
-        indicatif::ProgressBar::hidden().into()
+    fn from_indicatif(pb: indicatif::ProgressBar) -> Self {
+        let inner = Arc::new(pb);
+        logging::set_progress_bar(Some(Arc::downgrade(&inner)));
+        ProgressBar {
+            inner: Some(inner),
+            start: Instant::now(),
+            prefix: None,
+        }
+    }
+
+    fn no_progress_bar() -> Self {
+        ProgressBar {
+            inner: None,
+            start: Instant::now(),
+            prefix: None,
+        }
     }
 
     pub fn finish_with_duration(&self, op: &str) {
         let dur = self.start.elapsed();
         // We could use `dur.as_secs_f64()`, but its unnecessarily precise (micros). Millis are enough for our purpose.
         let msg = format!("{op} completed in {}s", dur.as_millis() as f64 / 1000.0);
-        let progress_style = ProgressStyle::default_bar().template("{prefix:.dim} {msg}");
-        self.inner.set_style(progress_style);
-        self.inner.set_prefix(">");
-        self.inner.finish_with_message(&msg);
-        logging::set_progress_bar(None);
+
+        if let Some(inner) = &self.inner {
+            let progress_style = ProgressStyle::default_bar().template("{prefix:.dim} {msg}");
+            inner.set_style(progress_style);
+            inner.set_prefix(">");
+            inner.finish_with_message(&msg);
+            logging::set_progress_bar(None);
+        } else {
+            log::info!("> {msg}");
+        }
     }
 
     pub fn finish_and_clear(&self) {
-        self.inner.finish_and_clear();
-        logging::set_progress_bar(None);
+        if let Some(inner) = &self.inner {
+            inner.finish_and_clear();
+            logging::set_progress_bar(None);
+        }
     }
-}
 
-impl From<indicatif::ProgressBar> for ProgressBar {
-    fn from(pb: indicatif::ProgressBar) -> Self {
-        let inner = Arc::new(pb);
-        logging::set_progress_bar(Some(Arc::downgrade(&inner)));
-        ProgressBar {
-            inner,
-            start: Instant::now(),
+    pub fn set_style(&self, style: ProgressStyle) {
+        if let Some(inner) = &self.inner {
+            inner.set_style(style);
+        }
+    }
+
+    pub fn set_message<S: AsRef<str>>(&self, msg: S) {
+        if let Some(inner) = &self.inner {
+            inner.set_message(msg.as_ref());
+        } else {
+            log::debug!(
+                "{}{}",
+                self.prefix
+                    .as_deref()
+                    .map(|s| format!("{s} "))
+                    .unwrap_or_default(),
+                msg.as_ref()
+            );
         }
     }
-}
 
-impl Deref for ProgressBar {
-    type Target = indicatif::ProgressBar;
+    pub fn tick(&self) {
+        if let Some(inner) = &self.inner {
+            inner.tick();
+        }
+    }
 
-    fn deref(&self) -> &Self::Target {
-        &self.inner
+    pub fn set_prefix<S: AsRef<str>>(&mut self, prefix: S) {
+        if let Some(inner) = &self.inner {
+            inner.set_prefix(prefix.as_ref());
+        } else {
+            self.prefix = Some(prefix.as_ref().to_owned());
+        }
+    }
+
+    pub fn set_position(&self, pos: u64) {
+        if let Some(inner) = &self.inner {
+            inner.set_position(pos);
+        }
+    }
+
+    pub fn inc(&self, delta: u64) {
+        if let Some(inner) = &self.inner {
+            inner.inc(delta);
+        }
+    }
+
+    pub fn enable_steady_tick(&self, interval: u64) {
+        if let Some(inner) = &self.inner {
+            inner.enable_steady_tick(interval);
+        }
     }
 }
 
diff --git a/tests/integration/_cases/debug_files/upload/debug_files-upload-mixed-embedded-sources.trycmd b/tests/integration/_cases/debug_files/upload/debug_files-upload-mixed-embedded-sources.trycmd
index 2bd43d4ac9..74bd2b1687 100644
--- a/tests/integration/_cases/debug_files/upload/debug_files-upload-mixed-embedded-sources.trycmd
+++ b/tests/integration/_cases/debug_files/upload/debug_files-upload-mixed-embedded-sources.trycmd
@@ -4,7 +4,10 @@ $ sentry-cli --log-level=debug debug-files upload --include-sources tests/integr
   INFO    [..] Loaded config from [CWD]/.sentryclirc
 ...
 > Found 1 debug information file (1 with embedded sources)
+  DEBUG   [..] > SrcGenSampleApp.pdb
+...
 > Resolved source code for 0 debug information files
+  DEBUG   [..] > SrcGenSampleApp.pdb
 > Prepared debug information file for upload
 ...