diff --git a/common/speculative.cpp b/common/speculative.cpp
index c99b19dbfd..84d2556ceb 100644
--- a/common/speculative.cpp
+++ b/common/speculative.cpp
@@ -805,6 +805,42 @@ enum common_speculative_type common_speculative_type_from_name(const std::string
     return it->second;
 }
 
+bool common_speculative_is_compat(llama_context * ctx_tgt) {
+    auto * mem = llama_get_memory(ctx_tgt);
+    if (mem == nullptr) {
+        return false;
+    }
+
+    bool res = true;
+
+    llama_memory_clear(mem, true);
+
+    // eval 2 tokens to check if the context is compatible
+    std::vector<llama_token> tmp;
+    tmp.push_back(0);
+    tmp.push_back(0);
+
+    int ret = llama_decode(ctx_tgt, llama_batch_get_one(tmp.data(), tmp.size()));
+    if (ret != 0) {
+        LOG_ERR("%s: llama_decode() failed: %d\n", __func__, ret);
+        res = false;
+        goto done;
+    }
+
+    // try to remove the last tokens
+    if (!llama_memory_seq_rm(mem, 0, 1, -1)) {
+        LOG_WRN("%s: the target context does not support partial sequence removal\n", __func__);
+        res = false;
+        goto done;
+    }
+
+done:
+    llama_memory_clear(mem, true);
+    llama_synchronize(ctx_tgt);
+
+    return res;
+}
+
 // initialization of the speculative decoding system
 //
 common_speculative * common_speculative_init(
diff --git a/common/speculative.h b/common/speculative.h
index 76fe6bb7bc..876cde3d18 100644
--- a/common/speculative.h
+++ b/common/speculative.h
@@ -14,6 +14,10 @@ enum common_speculative_type common_speculative_type_from_name(const std::string
 // convert type to string
 std::string common_speculative_type_to_str(enum common_speculative_type type);
 
+// check if the llama_context is compatible for speculative decoding
+// note: clears the memory of the context
+bool common_speculative_is_compat(llama_context * ctx_tgt);
+
 common_speculative * common_speculative_init(
         common_params_speculative & params,
         llama_context             * ctx_tgt);
diff --git a/tools/server/server-context.cpp b/tools/server/server-context.cpp
index 7f9c3c566b..b71d496eeb 100644
--- a/tools/server/server-context.cpp
+++ b/tools/server/server-context.cpp
@@ -740,6 +740,11 @@ private:
 
         slots.clear();
 
+        const bool can_spec = common_speculative_is_compat(ctx);
+        if (!can_spec) {
+            SRV_WRN("%s", "speculative decoding not supported by this context\n");
+        }
+
         // initialize slots
         for (int i = 0; i < params_base.n_parallel; i++) {
             server_slot slot;
@@ -752,7 +757,7 @@ private:
             slot.prompt.tokens.has_mtmd = mctx != nullptr;
 
             // try speculative decoding
-            {
+            if (can_spec) {
                 slot.spec = common_speculative_init(params_base.speculative, slot.ctx);
                 if (slot.spec) {
                     if (mctx) {